US2638478A - Phosphorus-containing derivatives of m-amino-phenols - Google Patents
Phosphorus-containing derivatives of m-amino-phenols Download PDFInfo
- Publication number
- US2638478A US2638478A US159858A US15985850A US2638478A US 2638478 A US2638478 A US 2638478A US 159858 A US159858 A US 159858A US 15985850 A US15985850 A US 15985850A US 2638478 A US2638478 A US 2638478A
- Authority
- US
- United States
- Prior art keywords
- methyl
- phosphate
- dimethylaminophenyl
- sulphate
- phenols
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 title description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 6
- -1 methyl sulphate anions Chemical class 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- 239000011734 sodium Substances 0.000 description 5
- 229910021653 sulphate ion Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QJCWEGKKEXEKCZ-UHFFFAOYSA-N P(=O)(OC1=CC(=CC=C1)N(C)C)(OC(C)C)OC(C)C Chemical compound P(=O)(OC1=CC(=CC=C1)N(C)C)(OC(C)C)OC(C)C QJCWEGKKEXEKCZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- GUFGWNUUDBGEGH-UHFFFAOYSA-N 2-[chloro(propan-2-yloxy)phosphoryl]oxypropane Chemical compound CC(C)OP(Cl)(=O)OC(C)C GUFGWNUUDBGEGH-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- PAIVEGSMGRDHOZ-UHFFFAOYSA-N [3-(dimethylamino)phenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)OC1=CC=CC(N(C)C)=C1 PAIVEGSMGRDHOZ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Definitions
- R is an alkyl or alkenyl group containing not more than four carbon atoms or an aralkyl group, e. g. a benzyl group
- X is a monovalent anion.
- Preferred monovalent anions are the chloride, bromide, iodide and methyl sulphate anions.
- the present specification also includes a process for the manufacture of dialkyl phosphates and alkyl alkyl (or aryl) phosphonates of mdimethylaminophenol of the general Formula I wherein m-dimethylaminophenol in the form of an alkali metal derivative is reacted with a dialkyl halogenophosphonate or an alkyl alkyl (or aryl) halogenophosphonite.
- dialkyl halogenophosphonate or an alkyl alkyl (or aryl) halogenophosphonite These compounds can be readily converted into their quaternary salts of general Formula II in a manner which is known per se.
- the quaternary compounds of the present invention have an anticholinesterase activity which renders them useful as pharmaceuticals. l
- dialkyl halogenophosphonate or the alkyl alkyl (or aryl) halogenophosphonite used as the reagent for the introduction of the phosphoruscontaim'ng radical into the m-aminophenol is preferably the chloro-compound.
- preferred reagents are:
- m-Dimethylaminophenyl-diethyl phosphate An ethanclic solution of the sodium salt of m-dimethylaminophenol is prepared by adding m-dimethylaminophenol (7.54 g., 0.055 M) to a solution -of sodium ethoxide, made by dissolving metallic sodium- (1.4 g., 0.061 M) in absolute ethanol (80 ml.), maintained in a nitrogen-atmosphere. Diethyl chlorophosphonate (10.51 g., 0.061 M) is added in one portion and the mixture is refluxed with stirrin for two hours.
- EXAMPLE 7 m..-DimethyZaminophenyZ-di-sec-butyl phosphate m-Dimethylaminophenol (6.9 g.) is dissolved in ethanolic" sodium" ethoxide (1.4 g. Na; ml. ethanol) in a nitrogen atmosphere and disecbutyl chlorophosphon'ate (13.7 g.) is added dropwiseoverzBQ minutes. The procedure is as in EX- ampl'e Theyield of m-dimethylaminophenyldij sec butyl phosphate is 62.5%; B. P. 119-124 C. 2122.3 x 111- to.. .8.x-.1()* mm.
- EXAMPLE 8 m flimethylaminophenyl dz sec butyl phosphate-methyZ-methyl sulphate
- a solution of' m-climethylaminophenyl di secbutyl'phosphate(1'.6'5" g;)' in dry benzene" (4' ml.) and dim-ethyl sulphate (0.7- ml.) is allowed to stand-"for 2 days.
- the preparation proceeds as in Example 4.
- Hyg'roscopio colorless plates offindimethyl'aminoph-enyl di-sec-butyl phosphatemethyFmethyY sulphate are obtained, M. P. 92 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Description
Patented May 12, 1953 UNITED STATE IIPHOSPHORUS-CONIAINING DERIVATIVES F M-AMIINO-PHENOLS' Alexander Lang Morrison and Frank Ratcliiife Atherton, signers to WelwynGarden City, England, as-
Hoffman'mLa Roche Inc., Nutley,
N. J a corporationof New Jersey No Drawing. Application May a, 1950, Serial No. 159,858. In Great Britain May 4, 1949 group containing not more than eight. carbon" atoms (including isoalkyl and oyclohexyl groups), R is an alkyl or alkenyl group containing not more than four carbon atoms or an aralkyl group, e. g. a benzyl group, and X is a monovalent anion. Preferred monovalent anions are the chloride, bromide, iodide and methyl sulphate anions.
The present specification also includes a process for the manufacture of dialkyl phosphates and alkyl alkyl (or aryl) phosphonates of mdimethylaminophenol of the general Formula I wherein m-dimethylaminophenol in the form of an alkali metal derivative is reacted with a dialkyl halogenophosphonate or an alkyl alkyl (or aryl) halogenophosphonite. These compounds can be readily converted into their quaternary salts of general Formula II in a manner which is known per se.
The quaternary compounds of the present invention have an anticholinesterase activity which renders them useful as pharmaceuticals. l
The dialkyl halogenophosphonate or the alkyl alkyl (or aryl) halogenophosphonite used as the reagent for the introduction of the phosphoruscontaim'ng radical into the m-aminophenol is preferably the chloro-compound. such preferred reagents are:
Dimethyl jchlorophosphonate Diethyl chlorophosphonate Di-(n or iso)-propyl chlorophosphonate Methyl methylchlorophosphonite v Ethyl ethylchlorophosphonite Ethyl phenylchlorophosphonite I The following examples illustrate how the process of the invention may be carried into effect.
Examples of m-Dimethylaminophenyl-diethyl phosphate An ethanclic solution of the sodium salt of m-dimethylaminophenol is prepared by adding m-dimethylaminophenol (7.54 g., 0.055 M) to a solution -of sodium ethoxide, made by dissolving metallic sodium- (1.4 g., 0.061 M) in absolute ethanol (80 ml.), maintained in a nitrogen-atmosphere. Diethyl chlorophosphonate (10.51 g., 0.061 M) is added in one portion and the mixture is refluxed with stirrin for two hours. After cooling, the precipitated sodium chloride is filtered and washed with alcohol and the filtrate is evaporated under reduced pressure. I The residual oil is 1 dissolved in carbon tetrachloride (50 ml.) and the solution is washed with sodium I hydroxide solution (3 x 40 m1. normal solution) andwater (3 x 40 ml.) After drying over potassium carbonate, the drying agent is filtered off and the filtrate evaporated under reduced pressure in a water pump. Distilled under mercury diffusion pump vacuum, the product boils at 1l6-120 C./3 x 10- mm. The yield of m-dimethyl aminophenyl-diethyl phosphate is 10.9 g. (='73%), n =1.5112.
EXAMPLE 2 m-Dimethylaminophenyl-di-isopropyl phosphate m-Dimethylaminophenyl di isopropyl phosphate is prepared in a manner similar to that of Example 1 from m-dimethylaminophenol (8.22 g., 0.06 M), sodium (1.65 g., 0.072 M), isopropyl alcohol (80 ml.) and di-isopropyl chlorophosphonate (14.37 g., 0.072 M). It boils at l10-1l4 C./1 x 10* mm. The yield of m-dimethylaminophenyl di isopropyl phosphate is 12.25 g. (=68%) n "=1.5102.
EXAMPLE 3 m-Dimethylamz'nophenyl-dimethyl phosphate m-Dimethylaminophenol (6.85 g.) is dissolved in ethanolic sodium ethoxide (1.25 g. Na; ml.
solved in carbon tetrachloride (ca. 50 ml.) and? the solution extracted three times with N/2 sodium hydroxide and three timesz;withxwazterz The: solution is dried over anhydrous sodiumsulphateand the. carbon tetrachloiiclev evaporated. in
vacuo. Distillation of the residualihrown 011 gives..- e. m--dimethylaminophenyl-dimethyl phosphate as a colorless-oil, in".
the required product, i.
50% yield; 13. P. 120123 C. at 0.05 mm.
EXAMPLE 4 m Dimethylamz'nophenyl dimethylphosphatew methyl-methyl sulphate A: solution of m--dimethyIaminoplienyl'-cli;--
methyl phosphate (1:..85 gr) in drybenzene (60 ml.) and dimethyl. sulphate (1 m1.) is allowed to stand for 30 hours at Ciduring'which. time the methylemethyl sulphate: crystallise's out. Ether is add'edfandjthe. crystals- P1 829 849 C.) are collected. The: yield amounts. to. 66%. Recrystallisation, from alool'lol ethyl. acetate-ether gives colorless plates of m diinethylamiriophenyldimetliylphosphateemethyl methylisulphate;- M. P. 8486 "C.'
EXAMPLE 5 m Dimethylaminoplienyl diethylphosphate methyl -methyl sulpiwte:
induced" tocrystallise'f-rom' alcohol-ethyl acetateether. The yield is M. P. 68-72 C. (deliquescent). Repeated recrystallisations give small colorless needles of m-dimethylaminophenyl-di-isopropyl phosphate methyl-methyl sulphate,.M. P. 82 8.4 C.
EXAMPLE 7 m..-DimethyZaminophenyZ-di-sec-butyl phosphate m-Dimethylaminophenol (6.9 g.) is dissolved in ethanolic" sodium" ethoxide (1.4 g. Na; ml. ethanol) in a nitrogen atmosphere and disecbutyl chlorophosphon'ate (13.7 g.) is added dropwiseoverzBQ minutes. The procedure is as in EX- ampl'e Theyield of m-dimethylaminophenyldij sec butyl phosphate is 62.5%; B. P. 119-124 C. 2122.3 x 111- to.. .8.x-.1()* mm.
EXAMPLE 8 m flimethylaminophenyl dz sec butyl phosphate-methyZ-methyl sulphate A solution of' m-climethylaminophenyl di secbutyl'phosphate(1'.6'5" g;)' in dry benzene" (4' ml.) and dim-ethyl sulphate (0.7- ml.) is allowed to stand-"for 2 days. The preparation proceeds as in Example 4. Hyg'roscopio colorless plates offindimethyl'aminoph-enyl di-sec-butyl phosphatemethyFmethyY sulphate are obtained, M. P. 92 C.
We claim:
1. A compound selectedfrom the group consisting of m-dimethylaminophenyl-di-lower alkyl phosphates and the quaternaryammonium salts thereof.
2. m-Dimethylaminophenyl diethyl phosphate.
3. m Dimethylamlnophenyldimethylphosphate-methyl-meth-yl sulphate.
4. m-Dimethylaminophenyl diethylphosphatemethyl-methyl-sulphate.
5. m-Dimethylaminophenyl-di-isopropyl phosphate methyl-methyl sulphate.
6. m-Dimethylaminophenyl-l-di-sec butyl phosphate-methyl-methyl sulphate.
ALEXANDER;v LANG MQRR'ISON. FRAIIK. ATI-IERTON.
References Citedin the file of this patent FOREIGN! PATENTS."
Number Country" Date Switzerland Maya, 1949
Claims (1)
1. A COMPOUND SELECTED FROM THE GROUP CONSISTING OF M-DIMETHYLAMINOPHENYL-DI-LOWER ALKYL PHOSPHATES AND THE QUATERNARY AMMONIUM SALTS THEREOF.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2638478X | 1949-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2638478A true US2638478A (en) | 1953-05-12 |
Family
ID=10912338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US159858A Expired - Lifetime US2638478A (en) | 1949-05-04 | 1950-05-03 | Phosphorus-containing derivatives of m-amino-phenols |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2638478A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2911430A (en) * | 1958-01-15 | 1959-11-03 | Campbell Pharmaceuticals Inc | Quaternary salts of dialkyl thiophosphate esters |
| US3134800A (en) * | 1957-10-21 | 1964-05-26 | Upjohn Co | Amino aromatic phosphonates and process of preparation |
| US3383194A (en) * | 1964-12-22 | 1968-05-14 | Fmc Corp | m-ureidophenyl esters of omicron, omicron-dimethyl phosphorothioic acid as herbicides |
| US4409143A (en) * | 1980-04-30 | 1983-10-11 | Ciba-Geigy Ag | Monoazo dyes containing phosphamic acid diester groups |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US257649A (en) * | 1882-05-09 | Windmill |
-
1950
- 1950-05-03 US US159858A patent/US2638478A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US257649A (en) * | 1882-05-09 | Windmill |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3134800A (en) * | 1957-10-21 | 1964-05-26 | Upjohn Co | Amino aromatic phosphonates and process of preparation |
| US2911430A (en) * | 1958-01-15 | 1959-11-03 | Campbell Pharmaceuticals Inc | Quaternary salts of dialkyl thiophosphate esters |
| US3383194A (en) * | 1964-12-22 | 1968-05-14 | Fmc Corp | m-ureidophenyl esters of omicron, omicron-dimethyl phosphorothioic acid as herbicides |
| US4409143A (en) * | 1980-04-30 | 1983-10-11 | Ciba-Geigy Ag | Monoazo dyes containing phosphamic acid diester groups |
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