Process to chloroketoamines using carbamates

Details Process to chloroketoamines using carbamates Process to chloroketoamines using carbamates

C - Chemistry, Metallurgy

07

C

C07C 233/76 (2006.01) C07C 221/00 (2006.01) C07C 225/04 (2006.01) C07C 231/02 (2006.01) C07C 233/31 (2006.01) C07C 235/46 (2006.01) C07C 253/30 (2006.01) C07C 255/57 (2006.01) C07C 319/20 (2006.01) C07C 323/52 (2006.01) C07D 213/82 (2006.01) C07D 263/38 (2006.01) C07D 263/52 (2006.01) C07D 307/68 (2006.01) C07D 333/38 (2006.01) C07C 225/06 (2006.01) C07C 225/10 (2006.01)

Patent

CA 2234132

The present invention relates to a process for preparing 5-methylene cyclic carbamates either by cyclization of an alkynyl amine with carbon dioxide in the presence of a copper catalyst or by forming an isocyanate from a substituted acetoacetamide followed by hydrolysis. The 5-methylene cyclic carbamates by either method are converted to 5-(chloromethylene) cyclic carbamates, using trichloroisocyanuric acid, followed by hydrolysis to a chloroketoamine. The chloroketoamine from the process of this invention additionally can be reacted with an organic acid chloride to form an amide compound which is useful as a fungicide.

L'invention concerne un processus de préparation de carbamates cycliques portant un groupe méthylène en position 5, soit par cyclisation d'une alkynylamine avec du gaz carbonique en présence d'un catalyseur de cuivre soit par formation d'un isocyanate à partir d'un acétoacétamide substitué suivie d'une hydrolyse. Les carbamates cycliques portant un groupe méthylène en position 5 obtenus par l'une ou l'autre méthode sont convertis en carbamates cycliques portant un groupe chlorométhylène en position 5, en utilisant de l'acide trichloroisocyanurique, lesquels sont hydrolysés en chlorocétoamines. Les chlorocétoamines du processus de cette invention peuvent aussi réagir avec un chlorure d'acide organique pour former des amides utiles comme fongicides.

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