US2557911A - Method of preparing glycocyamidines - Google Patents
Method of preparing glycocyamidines Download PDFInfo
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- US2557911A US2557911A US156933A US15693350A US2557911A US 2557911 A US2557911 A US 2557911A US 156933 A US156933 A US 156933A US 15693350 A US15693350 A US 15693350A US 2557911 A US2557911 A US 2557911A
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- octylglycocyamidine
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- 238000000034 method Methods 0.000 title claims description 10
- TYKJILJOXAHUFO-UHFFFAOYSA-N 2-amino-1,4-dihydroimidazol-5-one Chemical compound NC1=NC(=O)CN1 TYKJILJOXAHUFO-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- -1 for example Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VBOZZYDXKHSARC-UHFFFAOYSA-N phenylcyanamide;sodium Chemical compound [Na].N#CNC1=CC=CC=C1 VBOZZYDXKHSARC-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000005840 aryl radicals Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002178 crystalline material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 1
- OQUUVTMCNHHOQE-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC#N.[Na] Chemical compound ClC1=CC=C(C=C1)NC#N.[Na] OQUUVTMCNHHOQE-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ROJKPKOYARNFNB-UHFFFAOYSA-N Propyl pentanoate Chemical compound CCCCC(=O)OCCC ROJKPKOYARNFNB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N methyl propyl carbinol Natural products CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- KNVQTRVKSOEHPU-UHFFFAOYSA-N o-Chloroacetanilide Chemical compound CC(=O)NC1=CC=CC=C1Cl KNVQTRVKSOEHPU-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
Definitions
- R represents a member of the group consisting of alkyl and aryl radicals
- R represents a member of the group consisting, of hydrogen, alkyl and aryl radicals, such as, for example, l-n-butylglycocyamidine, l-n-octylglycocyamidine, l-dodecylglycocyamidine, l-octadecylglycocyamidine, l-phenylglycocyamidine, 1, 3- diphenylglycocyamidine, l-phenyl 3 ethylglycocyamidine, l-phenyl-3-allyglycocyamidine, 1- phenyl-3-cyclohexylglycocyamidine, 1-phenyl-3- n-octylglycocyamidine, l-phenyls3
- glycocyamidine of the above type maybe readily prepared by reacting an alkali-forming metal salt of. a monosubstituted cyanamide of the formula.
- M is an alkali-forming metal
- 2 is an integer not greater than 2 and R.
- R has the meaning shown above, with a haloacetamide of the formula X-CHi in which X is a halogen and R has the meaning shown above, in the presence of a solvent.
- alkali-forming metal as used in this specification and claims is intended to cover the alkali and alkaline earth metals.
- solvents which may be employed in the presses are water, the low molecular Weight aliphatic monohyclric alcohols such as, for example, methyl, ethyl, isopropy1,n-propyl, n-butyl, tert.-buty1 and sec.-amyl alcohol; ketones such as acetone, methy ethyl ketone, methyl n-propyl ketone, methyl isobutyl ketone, methyl benzyl ketone, cyclohexanone, and acetophenone; alkyl esters ofaliphatic monocarboxylic' acids having boiling points less than 200 C.
- the low molecular Weight aliphatic monohyclric alcohols such as, for example, methyl, ethyl, isopropy1,n-propyl, n-butyl, tert.-buty1 and sec.-amyl alcohol
- ketones such as acetone, meth
- n-capronitrile such as ethyl acetate, n-propyl acetate, n-butyl acetate, iso-butyl acetate, 2-ethylhexyl acetate, ethyl propionate, methyl butyrate and n-propyl valerate; aromatic nitriles and aliphatic saturated nitriles having boiling points not greater than 220 C. such as benzonitrile, acetonitrile, propionitrile, isobutyronitrile, and n-capronitrile.
- the reaction is preferably carried out at a temperature within the range of from about 20 to 0.. However, temperatures outside of this range may be employed depending upon the type of reactants and solvents utilized.
- Example 2 A mixture of 14 parts of sodium phenylcyanamide, 9.4 parts of chloroacetamide and 200 parts of acetone was heated to reflux for a period of 4 hours in a vessel equipped with a stirrer and refiux condenser. The mixture was cooled to room temperature and filtered. The filter cake was washed with water and then dried at 65 0., giving 9.1 parts of l-phenylglycocyamidine.
- Example 3 Example 2 was repeated using 200 parts of acetonitrile in place of the acetone as the solvent for the reactants. 10.6 parts of l-phenylglycocyamidine were obtained.
- Example 4 Example 2 was repeated using 200 parts of ethyl acetate in place of the acetone. 12.5 parts (71% yield) of l-phenylglycocyamidine were obtained.
- Example 5 A mixture of 4.4 parts of sodium n-octylcyanamide, 2.4 parts of chloroacetamide and 100 parts of acetone was heated to reflux for three The acetone was distilled on and the residue was washed with water to remove the by-product sodium chloride. 3.12 parts of l-noctylglycocyamidine were obtained. After recrystallization from alcohol, the product was a colorless crystalline material melting at 239"- 244" C.
- Example 6 A mixture of 14 parts of sodium phenylcyanamide, 25 parts of a-bromo-N-n-octylacetamide and 100 parts of ethyl alcohol was heated to reflux for two hours and then allowed to stand at room temperature for 16 hours. The reaction mixture was filtered to remove the precipitated sodium bromide. The filtrate was heated to distill off the ethyl alcohol. The residue was recrystallized twice from methyl alcohol, giving 8 parts of 1-phenyl-3-n-octylglycocyamidine, a colorless crystalline material melting at 3688 C.
- Example 7 A mixture of 14 parts of sodium phenylcyanamide, 17 parts of a-chloroacetanilide and 300 parts of acetone was warmed on a steam bath for one hour, then allowed to stand at room temperature for 48 hours. The acetone was distilled off, and the residue was washed with water and dried at 65 C. 22 parts (87% yield) of 1,3-diphenylglycocyamidine were obtained. After recrystallization from acetone, the product was a colorless crystalline material melting at 164-l65 C.
- Example 8 A mixture of 14 parts of sodium phenylcyanamide, 21.5 parts of a-chloro-p-nitroacetanilide and 150 parts of ethyl alcohol was heated to reflux for three hours and then allowed to stand at room temperature for 16 hours. The reaction mixture was filtered. The filter cake was washed with water and then dried, giving 23 parts (78% yield) of 1-pheny1-3-p-nitropheny1glycocyamidine. After recrystallization from acetone, the product was a yellow, crystallin material melting at 271-273 C.
- Example 9 8.73 parts of sodium-p-chlorophenylcyanamide and 4.68 parts of chloroacetamide were dissolved in parts of water and allowed to stand at room temperature for 48 hours. The resulting precipitate was filtered, washed with water and dried at C. 7 parts (67% yield) of l-p-chlorophenylglycocyamidine were obtained. After recrystallization from acetone, the product was a tan-colored, crystalline material melting at 275-278 C. with decomposition.
- glycocyamidines prepared by the methods of the present invention, are adapted for various uses, more particularly as chemotherapeutic agents, bactericides, and catalysts for the polymerization of unsaturated organic compounds to form high molecular weight linear polymers.
- a method of preparing a glycocyamidine of the general formula wherein R represents a member of the group consisting of alkyl and aryl radicals, and R represents a member of the group consisting of hydrogen, alkyl and aryl radicals, which comprises reacting an alkali-forming metal salt of a monosubstituted cyanamide of the formula RN M a in which M is an alkali-forming metal, a is an integer not greater than 2 and R is a member of the group consisting of alkyl and aryl radicals, with a haloacetamide of the formula X-CH C O r sen in which X is a halogen and R is a member of the group consisting of hydrogen, alkyl and aryl radicals, in the presence of a solvent, and recovering the glycocyamidine.
- a method of preparing l-phenylglycocyami- .dine which comprises reacting sodium phenylcyanamide withv chloroacetamide in the presence of a solvent, and recovering the 1-phenylglycocyamidine.
- a method of preparing l-n-octylglycocyamidine which comprises reacting sodium n-octylcyanamide with chloroacetamide in the presence of a solvent, and recovering the l-n-octylglycocyamidine.
- a method of preparing 1-phenyl-3-n-octylglycocyamidine which comprises reacting sodium phenylcyanamide with a-bromo-N-n-octylacetamide in the presence of a solvent, and recovering the 1-phenyl-3n-octylglycocyamidine.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Patented June 19, 1951 UNITED STATES PATENT OFFICE METHOD OF PREPARING GLYCO- CYAMIDIN ES Erick I. Hoegberg, Stamford, Conn., assignor to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application April 19, 1950, Serial No. 156,933
I eral formula HN=O2 4 \i/ in which R represents a member of the group consisting of alkyl and aryl radicals, and R represents a member of the group consisting, of hydrogen, alkyl and aryl radicals, such as, for example, l-n-butylglycocyamidine, l-n-octylglycocyamidine, l-dodecylglycocyamidine, l-octadecylglycocyamidine, l-phenylglycocyamidine, 1, 3- diphenylglycocyamidine, l-phenyl 3 ethylglycocyamidine, l-phenyl-3-allyglycocyamidine, 1- phenyl-3-cyclohexylglycocyamidine, 1-phenyl-3- n-octylglycocyamidine, l-phenyls3-decylglycocyamidine, l-n-amyl-3-isopropylglycocyamidine, 1- n-octyl-3-n-buty1g1ycocyamidine, l-n-octyl 3 tetradecylglycocyamidine, 1 -n-butyl-3 -(1-naphthyD-glycocyamidine, and l (2 ethylheXy1)-3- phenylglycocyamidine.
It has been discovered that a glycocyamidine of the above type maybe readily prepared by reacting an alkali-forming metal salt of. a monosubstituted cyanamide of the formula.
in which M is an alkali-forming metal, 2 is an integer not greater than 2 and R. has the meaning shown above, with a haloacetamide of the formula X-CHi in which X is a halogen and R has the meaning shown above, in the presence of a solvent.
The term alkali-forming metal as used in this specification and claims is intended to cover the alkali and alkaline earth metals.
A typical reaction in which sodium phenylcyanamide is reacted with a-blOIl'lO-N-Il-OCtYlacetamide to produce 1-phenyl-3 n octylglycocyamidine may be illustrated as follows:
Typical examples of solvents which may be employed in the presses are water, the low molecular Weight aliphatic monohyclric alcohols such as, for example, methyl, ethyl, isopropy1,n-propyl, n-butyl, tert.-buty1 and sec.-amyl alcohol; ketones such as acetone, methy ethyl ketone, methyl n-propyl ketone, methyl isobutyl ketone, methyl benzyl ketone, cyclohexanone, and acetophenone; alkyl esters ofaliphatic monocarboxylic' acids having boiling points less than 200 C. such as ethyl acetate, n-propyl acetate, n-butyl acetate, iso-butyl acetate, 2-ethylhexyl acetate, ethyl propionate, methyl butyrate and n-propyl valerate; aromatic nitriles and aliphatic saturated nitriles having boiling points not greater than 220 C. such as benzonitrile, acetonitrile, propionitrile, isobutyronitrile, and n-capronitrile.
The reaction is preferably carried out at a temperature within the range of from about 20 to 0.. However, temperatures outside of this range may be employed depending upon the type of reactants and solvents utilized.
The invention is further illustrated by the following examples in-which the parts areby weight.
Example 1 hours.
Example 2 A mixture of 14 parts of sodium phenylcyanamide, 9.4 parts of chloroacetamide and 200 parts of acetone was heated to reflux for a period of 4 hours in a vessel equipped with a stirrer and refiux condenser. The mixture was cooled to room temperature and filtered. The filter cake was washed with water and then dried at 65 0., giving 9.1 parts of l-phenylglycocyamidine.
Example 3 Example 2 was repeated using 200 parts of acetonitrile in place of the acetone as the solvent for the reactants. 10.6 parts of l-phenylglycocyamidine were obtained.
Example 4 Example 2 was repeated using 200 parts of ethyl acetate in place of the acetone. 12.5 parts (71% yield) of l-phenylglycocyamidine were obtained.
Example 5 A mixture of 4.4 parts of sodium n-octylcyanamide, 2.4 parts of chloroacetamide and 100 parts of acetone was heated to reflux for three The acetone was distilled on and the residue was washed with water to remove the by-product sodium chloride. 3.12 parts of l-noctylglycocyamidine were obtained. After recrystallization from alcohol, the product was a colorless crystalline material melting at 239"- 244" C.
Example 6 A mixture of 14 parts of sodium phenylcyanamide, 25 parts of a-bromo-N-n-octylacetamide and 100 parts of ethyl alcohol was heated to reflux for two hours and then allowed to stand at room temperature for 16 hours. The reaction mixture was filtered to remove the precipitated sodium bromide. The filtrate was heated to distill off the ethyl alcohol. The residue was recrystallized twice from methyl alcohol, giving 8 parts of 1-phenyl-3-n-octylglycocyamidine, a colorless crystalline material melting at 3688 C.
Example 7 A mixture of 14 parts of sodium phenylcyanamide, 17 parts of a-chloroacetanilide and 300 parts of acetone was warmed on a steam bath for one hour, then allowed to stand at room temperature for 48 hours. The acetone was distilled off, and the residue was washed with water and dried at 65 C. 22 parts (87% yield) of 1,3-diphenylglycocyamidine were obtained. After recrystallization from acetone, the product was a colorless crystalline material melting at 164-l65 C.
Example 8 A mixture of 14 parts of sodium phenylcyanamide, 21.5 parts of a-chloro-p-nitroacetanilide and 150 parts of ethyl alcohol was heated to reflux for three hours and then allowed to stand at room temperature for 16 hours. The reaction mixture was filtered. The filter cake was washed with water and then dried, giving 23 parts (78% yield) of 1-pheny1-3-p-nitropheny1glycocyamidine. After recrystallization from acetone, the product was a yellow, crystallin material melting at 271-273 C.
Example 9 8.73 parts of sodium-p-chlorophenylcyanamide and 4.68 parts of chloroacetamide were dissolved in parts of water and allowed to stand at room temperature for 48 hours. The resulting precipitate was filtered, washed with water and dried at C. 7 parts (67% yield) of l-p-chlorophenylglycocyamidine were obtained. After recrystallization from acetone, the product was a tan-colored, crystalline material melting at 275-278 C. with decomposition.
The glycocyamidines, prepared by the methods of the present invention, are adapted for various uses, more particularly as chemotherapeutic agents, bactericides, and catalysts for the polymerization of unsaturated organic compounds to form high molecular weight linear polymers.
While the invention has been described with particular reference to specific embodiments, it is to be understood that it is not to be limited thereto but is to be construed broadly and restricted solely by the scope of the appended claims.
I claim:
1. A method of preparing a glycocyamidine of the general formula wherein R represents a member of the group consisting of alkyl and aryl radicals, and R represents a member of the group consisting of hydrogen, alkyl and aryl radicals, which comprises reacting an alkali-forming metal salt of a monosubstituted cyanamide of the formula RN M a in which M is an alkali-forming metal, a is an integer not greater than 2 and R is a member of the group consisting of alkyl and aryl radicals, with a haloacetamide of the formula X-CH C=O r sen in which X is a halogen and R is a member of the group consisting of hydrogen, alkyl and aryl radicals, in the presence of a solvent, and recovering the glycocyamidine.
2. The method of claim 1 in which the reaction is .carried out at a temperature within the range of from about 20-150 C.
3. A method of preparing l-phenylglycocyami- .dine which comprises reacting sodium phenylcyanamide withv chloroacetamide in the presence of a solvent, and recovering the 1-phenylglycocyamidine.
4. A method of preparing l-n-octylglycocyamidine which comprises reacting sodium n-octylcyanamide with chloroacetamide in the presence of a solvent, and recovering the l-n-octylglycocyamidine.
5. A method of preparing 1-phenyl-3-n-octylglycocyamidine which comprises reacting sodium phenylcyanamide with a-bromo-N-n-octylacetamide in the presence of a solvent, and recovering the 1-phenyl-3n-octylglycocyamidine.
ERICK I. HOEGBERG.
No references cited.
7 Patent No. 2,557 ,911
Certificate of Correction June 19, 1951 ERICK I. HOEGBERG It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows:
Column 2, line 17, for presses read process;
and that the said Letters Patent should be read as corrected above, so that the same may conform to the record of the case in the Patent Oflice.
Signed and sealed this 28th day of August, A. D. 1951.
THOMAS F. MURPHY,
Assistant (Jommiasz'oner of Patents.
Claims (1)
1. A METHOD OF PREPARING A GLYCOCYAMIDINE OF THE GENERAL FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US156933A US2557911A (en) | 1950-04-19 | 1950-04-19 | Method of preparing glycocyamidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US156933A US2557911A (en) | 1950-04-19 | 1950-04-19 | Method of preparing glycocyamidines |
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| Publication Number | Publication Date |
|---|---|
| US2557911A true US2557911A (en) | 1951-06-19 |
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| US156933A Expired - Lifetime US2557911A (en) | 1950-04-19 | 1950-04-19 | Method of preparing glycocyamidines |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2161917A1 (en) * | 1971-10-21 | 1973-07-13 | American Cyanamid Co | |
| US4044021A (en) * | 1971-10-21 | 1977-08-23 | American Cyanamid Company | Tetrasubstituted imidazolidine diuretics useful in the treatment of hyperaldosteronism |
| US4110445A (en) * | 1972-10-02 | 1978-08-29 | American Cyanamid Company | Method for antagonizing aldosteronic action and inducing diuresis by administering a tetrasubstituted imidazolidine |
| FR2423485A1 (en) * | 1978-04-21 | 1979-11-16 | Egyt Gyogyszervegyeszeti Gyar | NEW SUBSTITUTED 1,3-DIARYL-2-IMINO-IMIDAZOLIDINES AND 1,3-DIARYL-2-IMINO-HEXAHYDRO-PYRIMIDINES, METHODS FOR THE PREPARATION OF THESE COMPOUNDS AND MEDICINAL PRODUCTS CONTAINING THEM |
-
1950
- 1950-04-19 US US156933A patent/US2557911A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2161917A1 (en) * | 1971-10-21 | 1973-07-13 | American Cyanamid Co | |
| US4044021A (en) * | 1971-10-21 | 1977-08-23 | American Cyanamid Company | Tetrasubstituted imidazolidine diuretics useful in the treatment of hyperaldosteronism |
| US4110445A (en) * | 1972-10-02 | 1978-08-29 | American Cyanamid Company | Method for antagonizing aldosteronic action and inducing diuresis by administering a tetrasubstituted imidazolidine |
| FR2423485A1 (en) * | 1978-04-21 | 1979-11-16 | Egyt Gyogyszervegyeszeti Gyar | NEW SUBSTITUTED 1,3-DIARYL-2-IMINO-IMIDAZOLIDINES AND 1,3-DIARYL-2-IMINO-HEXAHYDRO-PYRIMIDINES, METHODS FOR THE PREPARATION OF THESE COMPOUNDS AND MEDICINAL PRODUCTS CONTAINING THEM |
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