DD285599A5 - PROCESS FOR PREPARING SUBSTITUTED 4-AMINO-1,3-THIAZOLENE - Google Patents
PROCESS FOR PREPARING SUBSTITUTED 4-AMINO-1,3-THIAZOLENE Download PDFInfo
- Publication number
- DD285599A5 DD285599A5 DD33368889A DD33368889A DD285599A5 DD 285599 A5 DD285599 A5 DD 285599A5 DD 33368889 A DD33368889 A DD 33368889A DD 33368889 A DD33368889 A DD 33368889A DD 285599 A5 DD285599 A5 DD 285599A5
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- DD
- German Democratic Republic
- Prior art keywords
- substituted
- amino
- preparation
- thiazoles
- synthesis
- Prior art date
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- Thiazole And Isothizaole Compounds (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von substituierten * Ziel der Erfindung ist es, ein Verfahren zu entwickeln, das einen Zugang zu unterschiedlich substituierten * unter Umgehung bekannter Varianten ermoeglicht. Die substituierten * besitzen als potentielle biologisch aktive Verbindungen und als Zwischenprodukte in der Synthese Bedeutung. Erfindungsgemaesz koennen die substituierten * der allgemeinen Formel 3, in der R1 und R2, gleich oder verschieden, fuer substituierte oder unsubstituierte Alkyl- oder Benzylreste stehen, durch Umsatz von N-Nitroguanyl-dithiocarbimidsaeuremonoestern mit g-Halogencrotonsaeureestern mit entsprechendem Substituentenmuster in Gegenwart von Basen hergestellt werden.{* N-Nitroguanyl-dithiocarbimidsaeuremonoester, g-Halogencrotonsaeureester; Nitramin; intramolekulare Substitution}The invention relates to a process for the preparation of substituted * The aim of the invention is to develop a process that allows access to differently substituted *, bypassing known variants. The substituted * are important as potential biologically active compounds and as intermediates in the synthesis. According to the invention, the substituted * of the general formula 3 in which R1 and R2, identically or differently, are substituted or unsubstituted alkyl or benzyl radicals, can be prepared by reacting N-nitroguanyl-dithiocarbimic acid monoesters with g-halocrotroic acid esters having a corresponding substituent pattern in the presence of bases {* N-nitroguanyl-dithiocarbimide-acid monoester, g-halocrotroic acid ester; nitramine; intramolecular substitution}
Description
SIISII
- H2O- H 2 O
- HX- HX
substituierte oder unsubstituierte Alkyl- oder Benzylreste stehen, durch Umsatz von N-Nitroguanyldithiocarbimidsäuremonoestem der Formel 1, in der R1 obige Bedeutung hat, mit Y-Halogencrotonsäureestern der Formel 2, in der X für ein beliebiges Halogen steht und R2 obige Bedeutung hat, in Gegenwart von Basen wie Kaliumhydroxid odersubstituted or unsubstituted alkyl or benzyl radicals, by conversion of N-Nitroguanyldithiocarbimidsäuremonoestem of formula 1, in which R 1 has the above meaning, with Y-halocrotonic acid esters of the formula 2, in which X is an arbitrary halogen and R 2 has the above meaning, in the presence of bases such as potassium hydroxide or
liegen zwischen 20°C und 80°C. Die Finalprodukte werden durch Eingießen der Reaktionslösung in Wasser gewonnen. Nach demlie between 20 ° C and 80 ° C. The final products are obtained by pouring the reaction solution in water. After this
und besitzen Bedeutung als Zwischenverbindungen für die Darstellung von Pharmaka und Pflanzenschutzmitteln.and have significance as intermediates for the presentation of pharmaceuticals and pesticides.
1. trans-3-(4-Amino-2-methylthio-5-thiazolyl)-acrylsäuremethylester1. Trans-3- (4-amino-2-methylthio-5-thiazolyl) -acrylic acid methyl ester
Mail löst 0,02mol N-Nitroguanyl-dithiocarbimidsäuremethylester in 30ml DMF und fügt unter Rühren 0,02mol KOH in 5ml Wasser gelöst hinzu. Zu der klaren Lösung gibt man tropfenweise 0,02 mol γ-Bromcrotonsäuromethylester ohne Kühlung. Nach Abklingen der exothermen Reaktion tropft man unter ständigem Rühren 2ml Triethylamin zur Reaktionsmischung und rührt weitere 30 Minuten bei etwa 5O0C. Die nach dem Ein jießen der Reaktionslösung in Wasser ausfallenden gelbbraunen Kristalle werden durch Umkristallisation aus Ethanol gereingtMail dissolves 0.02 mol of N-nitroguanyl-dithiocarbimic acid methyl ester in 30 ml of DMF and, while stirring, adds 0.02 mol of KOH dissolved in 5 ml of water. 0.02 mol of γ-Bromcrotonsäuromethylester without cooling to the clear solution is added dropwise. After the exothermic reaction is added dropwise with constant stirring 2 ml of triethylamine to the reaction mixture and stirred for another 30 minutes at about 5O 0 C. The reaction solution jießen after the A in water precipitating a tan crystals are purified by recrystallization from ethanol
Fp.: 157-8CC (Lit. 1520C) Ausbeute: 4,4 g (95,4% d. Th.)M.p .: 157-8 C C (Lit. 152 0 C) Yield: 4.4 g (95.4% of theory.).
2. trans-3-(4-Amino-2-ethylthio-5-thiazolyl)-acrylsäuremethylester2. trans-3- (4-amino-2-ethylthio-5-thiazolyl) -acrylic acid methyl ester
umgesetzt.implemented.
2 ή 5 S S 9 ' 3 2 ή 5 SS 9 ' 3
O2N-N=CO 2 NN = C
NH2 NH 2
X-CH,-CH=CH-C00R2 X-CH, -CH = CH-C00R 2
π2|Ν jr—N R2OOC-CH=CH-A5J-SR1 π 2 | Ν jr-NR 2 OOC-CH = CH-A 5 J-SR 1
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DD33368889A DD285599A5 (en) | 1989-10-18 | 1989-10-18 | PROCESS FOR PREPARING SUBSTITUTED 4-AMINO-1,3-THIAZOLENE |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DD33368889A DD285599A5 (en) | 1989-10-18 | 1989-10-18 | PROCESS FOR PREPARING SUBSTITUTED 4-AMINO-1,3-THIAZOLENE |
Publications (1)
Publication Number | Publication Date |
---|---|
DD285599A5 true DD285599A5 (en) | 1990-12-19 |
Family
ID=5613100
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD33368889A DD285599A5 (en) | 1989-10-18 | 1989-10-18 | PROCESS FOR PREPARING SUBSTITUTED 4-AMINO-1,3-THIAZOLENE |
Country Status (1)
Country | Link |
---|---|
DD (1) | DD285599A5 (en) |
-
1989
- 1989-10-18 DD DD33368889A patent/DD285599A5/en not_active IP Right Cessation
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