Synthesis of 2-phenylimino-1,3-thiazoline hydrochloride salts

2-Phenylimino-1,3-thiazoline 염산염 유도체의 합성

A synthesis of new 2-phenylimino-1,3-thiazolines 2 for the purpose of development of new agrochemical fuugicide was described. Reaction of chlorine with diketene followed by treatment of benzylamine without isolation of intermediate 8a gave ${\gamma}-chloro-{\beta}-keto$ benzylamide 10a. Thioureas 4 obtained from the reaction of methyl isothiocyanate with aniline derivatives were subjected to 10a in acetone solution to afford the corresponding 2-phenylimino-1,3-thiazoline hydrochloric acid salts 2 through unisolable inltermediates 11 and 12. The plausible reaction mechanism including nucleophilic attack of sulfur assisted neighboring nitrogen lone pair electron on phenyl of thiourea 4 was discussed.

새로운 살균제를 개발할 목적으로 새로운 2-phenylimino-1,3-thiazoline 유도체를 합성하였다. Ketone dimer를 염소와 반응시킨 다음 중간체 8a의 분리없이 benzylamine으로 처리하여 ${\gamma}-Chloro-{\beta}-keto$ benzylamide 10a를 얻었다. Methyl isothiocyanate와 aniline 유도체의 반응에서 얻은 thiourea 4를 10a와 acetone 용액 중에서 반응시켜 분리 불가능한 중간체 11 및 12를 거쳐 각각에 상응하는 2-phenylimino-1,3-thiazoline 유도체의 염산염 2를 얻었다. Thiourea 4의 phenyl기에 인접한 질소원자의 비공유 전자쌍의 도움으로 황원자의 친핵적 공격을 포함한 가능한 반응 mechanism을 논의하였다.