Arbeiten über Phosphorsäure- und Thiophosphorsäureester mit einem heterocyclischen Substituenten. 5. Mitteilung. 2-Alkoxy- und 2-Alkylthio-5-chlormethy1--1, 3,4-thiadiazole, 2-Alkyl- 5-chlormethy1-1,3,4-oxadiazole und daraus hergestellte Thio- und Dithiophosphorsäure-O, O-dialkyl-S-[(2-alkoxy- und 2-alkylthio-1, 3, 4- thiadiazol-5-yl)-methyl]- bzw. -S-[(2-alky1-1, 3, 4-oxadiazol-5-yl)-methyl-ester

✍ Scribed by K. Rüfenacht

• Publisher: John Wiley and Sons
• Year: 1972
• Tongue: German
• Weight: 436 KB
• Volume: 55
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19720550616

✦ Synopsis

Abstract

2‐Alkoxy‐5‐chloromethy1‐1,3,4‐thiadiazoles are prepared by ring closure of 3‐chloroacetyl‐thiocarbazic acid O‐alkyl esters with concentrated sulfuric acid, 2‐alkylthio‐5‐chloro‐methy1‐1,3,4‐thiadiazoles directly from dithiocarbazic acid alkylesters with chloroacetylchloride in benzene in a one step synthesis omitting the 3‐chloroacetyl‐derivatives and 2‐alkyl‐5‐chloro‐methy1‐1,3,4‐oxadiazoles from 1‐chloroacetyl‐2‐acyl‐hydrazines with POCl^3^. These three types of chloromethyl heterocycles easily react with salts of thio‐ and dithiophosphoric acids to form the corresponding O,O‐dialkyl‐S‐[(2‐alkoxy‐ and 2‐alkylthio‐1,3,4‐thiadiazol‐5‐yl)‐methyl]‐ and ‐S‐[(2‐alky1‐1,3,4‐oxadiazol‐5‐yl)‐methyl]‐thio‐ and ‐dithiophosphates.