DE4322053A1 - Process for the preparation of amino-substituted thioethers - Google Patents
Process for the preparation of amino-substituted thioethersInfo
- Publication number
- DE4322053A1 DE4322053A1 DE19934322053 DE4322053A DE4322053A1 DE 4322053 A1 DE4322053 A1 DE 4322053A1 DE 19934322053 DE19934322053 DE 19934322053 DE 4322053 A DE4322053 A DE 4322053A DE 4322053 A1 DE4322053 A1 DE 4322053A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- methyl
- oxazolidine
- oxo
- mercaptoethanol
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 amino-substituted thioethers Chemical class 0.000 title description 3
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 claims description 3
- NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ARILQDNHZGKJBK-UHFFFAOYSA-N Resedine Natural products O1C(=O)NCC1C1=CC=CC=C1 ARILQDNHZGKJBK-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JGXSWAULHGGZFZ-UHFFFAOYSA-N 3,4-diphenyl-1,3-oxazolidin-2-one Chemical compound O=C1OCC(C=2C=CC=CC=2)N1C1=CC=CC=C1 JGXSWAULHGGZFZ-UHFFFAOYSA-N 0.000 description 1
- WDQBSTXNKZZKTB-UHFFFAOYSA-N 3,5-diphenyl-1,3-oxazolidin-2-one Chemical compound O=C1OC(C=2C=CC=CC=2)CN1C1=CC=CC=C1 WDQBSTXNKZZKTB-UHFFFAOYSA-N 0.000 description 1
- DBVTYDLZMXNRIN-UHFFFAOYSA-N 3-benzyl-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1CC1=CC=CC=C1 DBVTYDLZMXNRIN-UHFFFAOYSA-N 0.000 description 1
- JWVAHTLOLKDVBE-UHFFFAOYSA-N 4-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-one Chemical compound OCC1COC(=O)N1C1=CC=CC=C1 JWVAHTLOLKDVBE-UHFFFAOYSA-N 0.000 description 1
- CRHQYASHOICRND-UHFFFAOYSA-N 4-ethyl-1,3-oxazolidin-2-one Chemical compound CCC1COC(=O)N1 CRHQYASHOICRND-UHFFFAOYSA-N 0.000 description 1
- QDMNNMIOWVJVLY-UHFFFAOYSA-N 4-phenyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)NC1C1=CC=CC=C1 QDMNNMIOWVJVLY-UHFFFAOYSA-N 0.000 description 1
- HBRXQSHUXIJOKV-UHFFFAOYSA-N 5-methyl-1,3-oxazolidin-2-one Chemical compound CC1CNC(=O)O1 HBRXQSHUXIJOKV-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
Die Erfindung betrifft ein neues Verfahren zur Herstellung von aminosubstituierten Thioethern. Derartige Verbindungen und ihre Herstellung sind grundsätzlich bekannt aus Journal of Medicinal and Chemistry, 1977, Vol. 20, Soloway, Chemo-Imuno- Therapie of Cancer, S. 1357 f. Aus J.Org. Chem. 1992, 57, Poindexter, S. 6257-6265 ist weiterhin die Verwendung von 2-Oxazolidinonen zur Aminoethylierung aromati scher Verbindungen bekannt.The invention relates to a new process for the preparation of amino-substituted Thioethers. Such connections and their production are known in principle from Journal of Medicinal and Chemistry, 1977, Vol. 20, Soloway, Chemo-Imuno- Therapy of Cancer, p. 1357 f. From J.Org. Chem. 1992, 57, Poindexter, pp. 6257-6265 is also the use of 2-oxazolidinones for aminoethylation aromati known connections.
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Verbindungen der allgemeinen Formel (I)The present invention relates to a method for producing compounds of the general formula (I)
worin
R, R¹-R⁴ unabhängig voneinander Wasserstoff, C₁-C₄-Alkyl, mit OH, C₁-C₄-
Alkoxy oder SO₃H-substituiertes C₁-C₄-Alkyl, Phenyl, Benzyl, mit Halogen,
C₁-C₄-Alkoxy oder SO₃H-substituiertes Phenyl oder Benzyl bedeuten,
dadurch gekennzeichnet, daß man von 2-Mercaptoethanol mit Verbindungen der
allgemeinen Formel (II)wherein
R, R¹-R⁴ independently of one another hydrogen, C₁-C₄-alkyl, with OH, C₁-C₄- alkoxy or SO₃H-substituted C₁-C₄-alkyl, phenyl, benzyl, with halogen, C₁-C₄-alkoxy or SO₃H-substituted phenyl or benzyl,
characterized in that 2-mercaptoethanol with compounds of the general formula (II)
worin
R und R¹-R⁴ die oben angegebene Bedeutung besitzen, umsetzt.wherein
R and R¹-R⁴ have the meaning given above, implemented.
Die Umsetzung erfolgt vorzugsweise bei Temperaturen zwischen 100°C und 250°C, vorzugsweise zwischen 150°C und 200°C.The reaction is preferably carried out at temperatures between 100 ° C and 250 ° C, preferably between 150 ° C and 200 ° C.
Bevorzugt wird das Verfahren zur Herstellung von Verbindungen der Formel (I),
worin
R = Wasserstoff, Methyl, Ethyl, Phenyl, Benzyl,
R¹-R⁴ = unabhängig voneinander Wasserstoff, Methyl, Phenyl ist.Preferred is the process for the preparation of compounds of formula (I), wherein
R = hydrogen, methyl, ethyl, phenyl, benzyl,
R¹-R⁴ = independently of one another is hydrogen, methyl, phenyl.
In einer besonders bevorzugten Ausführungsform haben R¹-R⁴ die gleiche Bedeutung.In a particularly preferred embodiment, R¹-R⁴ have the same Meaning.
Die Umsetzung wird in einem Lösungsmittel, bevorzugt aber ohne Lösemittel, durchgeführt.The reaction is carried out in a solvent, but preferably without a solvent, carried out.
Die Umsetzung von 2-Oxazolidinonen mit Thiophenolen ist zwar bekannt, mit Alkyl mercaptanen ist dagegen keine Umsetzung zu den 2-(Alkylmercapto)-ethylaminen gelungen (G.S. Poindexter et al., J. Org. Chem. 1992, 57, 6257-6265).The reaction of 2-oxazolidinones with thiophenols is known, with alkyl In contrast, mercaptans is not a conversion to the 2- (alkylmercapto) ethylamines succeeded (G.S. Poindexter et al., J. Org. Chem. 1992, 57, 6257-6265).
Die Verbindungen der Formel (II) sind z. T. bekannt, ihre Herstellung erfolgt nach Verfahren, wie sie beschrieben sind in Houben-Weyl, Bd. E4 (1983) S. 192-211. The compounds of formula (II) are e.g. T. known, their manufacture takes place after Methods as described in Houben-Weyl, Vol. E4 (1983) pp. 192-211.
Geeignet sind z. B.:
1-Oxo-1,3-oxazolidin (2-Oxazolidinon),
5-Methyl-2-oxo-1,3-oxazolidin,
3-Methyl-2-oxo-1,3-oxazolidin,
3-Phenyl-2-oxo-1,3-oxazolidin,
3-Benzyl-2-oxo-1,3-oxazolidin,
4-Phenyl-2-oxo-1,3-oxazolidin,
5-Phenyl-2-oxo-1,3-oxazolidin,
3,4-Diphenyl-2-oxo-1,3-oxazolidin ,
3,5-Diphenyl-2-oxo-1,3-oxazolidin,
3,4-Dimethy1-5-phenyl-2-oxo-1,3-oxazolidin,
3-Phenyl-4-hydroxymethyl-2-oxo-1,3-oxazolidin,
3,5-Dimethyl-2-oxo-1,3-oxazolidin
3-Ethyl-2-oxo-1,3-oxazolidin,
4-Ethyl-2-oxo-1,3-oxazolidin.Are suitable for. B .:
1-oxo-1,3-oxazolidine (2-oxazolidinone),
5-methyl-2-oxo-1,3-oxazolidine,
3-methyl-2-oxo-1,3-oxazolidine,
3-phenyl-2-oxo-1,3-oxazolidine,
3-benzyl-2-oxo-1,3-oxazolidine,
4-phenyl-2-oxo-1,3-oxazolidine,
5-phenyl-2-oxo-1,3-oxazolidine,
3,4-diphenyl-2-oxo-1,3-oxazolidine,
3,5-diphenyl-2-oxo-1,3-oxazolidine,
3,4-dimethy1-5-phenyl-2-oxo-1,3-oxazolidine,
3-phenyl-4-hydroxymethyl-2-oxo-1,3-oxazolidine,
3,5-dimethyl-2-oxo-1,3-oxazolidine
3-ethyl-2-oxo-1,3-oxazolidine,
4-ethyl-2-oxo-1,3-oxazolidine.
Als Lösemittel können alle die verwendet werden, deren pKS-Wert deutlich geringer ist als der des 2-Mercaptoethanols, und die nicht selbst mit 2-Mercaptoethanol reagieren, z. B. Kohlenwasserstoffe, Ether, Alkohole, Carbonsäureamide, Sulfoxide, Sulfone, ausgenommen sind Amine.As solvents, all of which are used whose pK is much lower than that of the 2-mercaptoethanol, and do not themselves react with 2-mercaptoethanol, z. B. hydrocarbons, ethers, alcohols, carboxamides, sulfoxides, sulfones, except amines.
Solche Lösemittel sind z. B. Mesitylen, Naphthalin, 1-Methylnaphthalin, 2-Methyl naphthalin, Dekalin, Tetralin, o-Dichlorbenzol, Nitrobenzol, Biphenyl, Diphenylether, 1-Hexanol, 1-Heptanol, 1-Octanol, 2-Octanol, Ethylenglykol, Diethylenglykol, Diethylenglykolmonomethylether, Diethylenglykolmonoethylether, Glyzerin, N- Methyl-pyrrolidon, Caprolactam, N-Methylcaprolactam, Cyclohexanol, Dimethylsulf oxid, Dimethylsulfon, Sulfolan.Such solvents are e.g. B. mesitylene, naphthalene, 1-methylnaphthalene, 2-methyl naphthalene, decalin, tetralin, o-dichlorobenzene, nitrobenzene, biphenyl, diphenyl ether, 1-hexanol, 1-heptanol, 1-octanol, 2-octanol, ethylene glycol, diethylene glycol, Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, glycerin, N- Methyl pyrrolidone, caprolactam, N-methyl caprolactam, cyclohexanol, dimethyl sulfate oxide, dimethyl sulfone, sulfolane.
Die erfindungsgemäß hergestellten 2-(2′-Aminoethylmercapto)-ethanole können verwendet werden als Zwischenprodukte für Pharmazeutika, Pestizide, insbesondere aber für Farbstoffe.The 2- (2'-aminoethylmercapto) ethanols prepared according to the invention can are used as intermediates for pharmaceuticals, pesticides, in particular but for dyes.
78, 1 g 2-Mercaptoethanol und 163 g 3-Phenyl-2-oxazolidinon werden unter N₂ 5
Stunden auf 160°C erhitzt. Man erhält 2-(2′-Phenylaminoethylmercapto)-ethanol in
fast quantitativer Ausbeute als schwach gelbliches Öl, dessen H-NMR-Spektrum
folgende Signale aufweisen: (Lösemittel D₆-DMSO)
δ 2,58-2,75 ppm, 6H, m, δ 3,22 ppm, 2H, t, δ 4,80 ppm, 1H, s; δ 6,50-6,61 ppm, 3H,
m; δ 7,05 ppm, 2H, d.78, 1 g of 2-mercaptoethanol and 163 g of 3-phenyl-2-oxazolidinone are heated to 160 ° C. under N₂ for 5 hours. 2- (2′-Phenylaminoethylmercapto) ethanol is obtained in almost quantitative yield as a slightly yellowish oil, the H-NMR spectrum of which shows the following signals: (solvent D₆-DMSO)
δ 2.58-2.75 ppm, 6H, m, δ 3.22 ppm, 2H, t, δ 4.80 ppm, 1H, s; δ 6.50-6.61 ppm, 3H, m; δ 7.05 ppm, 2H, d.
156,2 g 2-Mercaptoethanol und 202 g 3-Methyl-2-oxazolidinon werden unter N₂ 5 Stunden auf 160°C erhitzt. Das 2-(2′-Methylaminoethylmercapto)-ethanol wird unter vermindertem Druck destilliert. Man erhält ein farbloses Öl; Kp 5-6,5 mm = 124°C bis 130°C.156.2 g of 2-mercaptoethanol and 202 g of 3-methyl-2-oxazolidinone are under N₂ 5th Heated to 160 ° C for hours. The 2- (2'-methylaminoethylmercapto) ethanol is under distilled under reduced pressure. A colorless oil is obtained; Kp 5-6.5 mm = 124 ° C to 130 ° C.
78, 1 g 2-Mercaptoethanol und 87 g 2-Oxazolidinon werden in 100 ml Diethylen glykolmonometyhlether 5 Stunden zum Sieden erhitzt. Man destilliert zunächst das Lösemittel und dann das 2-(2′-Aminoethylmercapto)-ethanol unter vermindertem Druck; Kp 3 mm = 117°C bis 119°C.78, 1 g of 2-mercaptoethanol and 87 g of 2-oxazolidinone are in 100 ml of diethylene glycol monomethyl ether heated to boiling for 5 hours. You distill that first Solvent and then the 2- (2'-aminoethylmercapto) ethanol under reduced Print; Kp 3 mm = 117 ° C to 119 ° C.
Claims (5)
R, R¹-R⁴ unabhängig voneinander Wasserstoff, C₁-C₄-Alkyl, mit OH, C₁-C₄- Alkoxy oder SO₃H-substituiertes C₁-C₄-Alkyl, Phenyl, Benzyl, mit Halogen, C₁-C₄-Alkoxy oder SO₃H-substituiertes Phenyl oder Benzyl bedeuten,
dadurch gekennzeichnet, daß man 2-Mercaptoethanol mit Verbindungen der allgemeinen Formel (II) worin
R und R¹-R⁴ die oben angegebene Bedeutung besitzen, umsetzt.1. Process for the preparation of compounds of the general formula (1) wherein
R, R¹-R⁴ independently of one another hydrogen, C₁-C₄-alkyl, with OH, C₁-C₄- alkoxy or SO₃H-substituted C₁-C₄-alkyl, phenyl, benzyl, with halogen, C₁-C₄-alkoxy or SO₃H-substituted phenyl or benzyl,
characterized in that 2-mercaptoethanol with compounds of the general formula (II) wherein
R and R¹-R⁴ have the meaning given above, implemented.
R = Wasserstoff, Methyl, Ethyl, Phenyl, Benzyl,
R¹-R⁴ = unabhängig voneinander Wasserstoff, Methyl, Phenyl ist.2. The method according to claim 1, characterized in that
R = hydrogen, methyl, ethyl, phenyl, benzyl,
R¹-R⁴ = independently of one another is hydrogen, methyl, phenyl.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19934322053 DE4322053A1 (en) | 1993-07-02 | 1993-07-02 | Process for the preparation of amino-substituted thioethers |
| TW083105060A TW280812B (en) | 1993-07-02 | 1994-06-03 | |
| EP94109543A EP0632022B1 (en) | 1993-07-02 | 1994-06-21 | Process for the preparation of amino-substituted thioethers |
| DE59401383T DE59401383D1 (en) | 1993-07-02 | 1994-06-21 | Process for the preparation of amino substituted thioethers |
| US08/265,525 US5410081A (en) | 1993-07-02 | 1994-06-24 | Process for the preparation of amino-substituted thioethers |
| JP6165760A JPH0717946A (en) | 1993-07-02 | 1994-06-27 | Preparation of amino-substituted thioether |
| KR1019940015725A KR100286845B1 (en) | 1993-07-02 | 1994-07-01 | Process for preparing amino-substituted thioether |
| CN94108118A CN1038127C (en) | 1993-07-02 | 1994-07-02 | Process for the preparation of amino-substituted thioethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19934322053 DE4322053A1 (en) | 1993-07-02 | 1993-07-02 | Process for the preparation of amino-substituted thioethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4322053A1 true DE4322053A1 (en) | 1995-01-12 |
Family
ID=6491796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19934322053 Withdrawn DE4322053A1 (en) | 1993-07-02 | 1993-07-02 | Process for the preparation of amino-substituted thioethers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE4322053A1 (en) |
-
1993
- 1993-07-02 DE DE19934322053 patent/DE4322053A1/en not_active Withdrawn
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