Nippon Soda Co., Ltd.

Asubio Pharma Co. Ltd.

Daiichi Asubio Pharma Co., Ltd.

Mitsuru Takase

Fuminori Komatsu

Takahiro Sagae

Shigeo Mori

Shiro Tsubokura

Fumihiko Nagasaki

Daisuke Asanuma

Satoru Yamazaki

Yasuyuki Miyazawa

Kimihiko Oohata

Noriaki Kawahara

Hiroyuki Yazaki

Toshiyuki Watai

Hiroaki Shibasaki

Yutaka Ishii

A method for producing N-(2-amino-1,2-dicyanovinyl)imidates represented by the following formula (1-III) under low temperature conditions within a short period of time in high yield is provided. In addition, a method for producing N-(2-amino-1,2-dicyanovinyl)formamidine represented by the following formula (2-II) which is suitably applicable to a cyclization reaction for producing AlCN, AlCA or the like and which enhances yield of the cyclization reaction is provided. In addition, a method for producing aminoimidazole derivatives represented by the following formula (3-V) in high yield by using diaminomaleonitrile as a starting material is provided. 

Method for production of N-(2-amino-1,2-dicyanovinyl)imidates, method for production of N-(2-amino-1,2-dicyanovinyl)formamidine, and method for production of aminoimidazole derivatives

A method for producing N-(2-amino-1,2-dicyanovinyl)imidates represented by the following formula (1-III) under low temperature conditions within a short period of time in high yield is provided. In addition, a method for producing N-(2-amino-1,2-dicyanovinyl)formamidine represented by the following formula (2-II) which is suitably applicable to a cyclization reaction for producing AICN, AICA or the like and which enhances yield of the cyclization reaction is provided. In addition, a method for producing aminoimidazole derivatives represented by the following formula (3-V) in high yield by using diaminomaleonitrile as a starting material is provided. 

A method for producing N-(2-amino-1,2-dicyanovinyl)formamidine, including the steps of reacting an N-(2-amino-1,2-dicyanovinyl)formimidate and ammonia by adding aqueous ammonia to a solution or suspension of an N-(2-amino-1,2-dicyanovinyl)formimidate in ether, or alternatively directly adding an N-(2-amino-1,2-dicyanovinyl)formimidate or adding a solution or suspension of an N-(2-amino-1,2-dicyanovinyl)formimidate in ether to a liquid containing ether and aqueous ammonia.

The present invention provides a method for preparing an organic compound, which comprises a dehydration step of distilling off water from a polar organic solvent solution containing the organic compound and water to bring the concentration of water below a given level, wherein the dehydration step comprises distilling off water together with the polar organic solvent while adding a polar organic solvent to the solution, or comprises repeating several cycles of adding a polar organic solvent to the solution and then distilling off water together with the polar organic solvent. The present invention further provides the preparation of an organic compound, which enables efficient isolation of the target product in high isolated yield from a polar organic solvent solution containing the organic compound, water and, if necessary, a compound which produces, upon coming into contact with water or the like, a substance accelerating the decomposition of the organic compound.

Processes for preparation of organic compounds

There is provided a method by which various compounds (1) having a carboxyl group in the molecule have the carboxyl group converted to a (dioxolenon-4-yl)methyl ester at low cost, in a simple way and at high yield. The process for producing compounds of formula (3) according to the reaction scheme shown below comprises reacting carboxylic acids of formula (1) with 4-chloromethyldioxolenone compounds of formula (2) in a solvent in the presence of both a phase transfer catalyst and a metal iodide: [where Q represents an organic group, M represents a hydrogen atom, an alkali metal, an alkaline earth metal or a transition metal, Rand Rrepresent a hydrogen atom, an optionally substituted (Calkyl group or phenyl group)].

Process for producing (dioxolenon-4-yl)methyl ester derivative

The invention provides novel processes for preparing efficiently compounds of general formula (1) (wherein R1 and R2 are each independently hydrogen, optionally substituted C1-C10 alkyl, C3-C14 hydrocarbyl bearing alicyclic skeleton, or the like) and initermediates thereof. Compounds of general formula (I) can be prepared by subjecting compounds of general formula (II) and/or salts thereof to cyclization hydrolysis in an aqueous basic solution. Further, compounds of general formula (II) can be prepared from industrially easily available diaminomaleonitrile in a high yield.

Processes for the preparation of 4(5)-amino-5(4)-carboxamidoimidazoles and intermediates thereof

Compounds having one or more structures represented by general formula (I) as partial structure thereof, which are typified by pyrimidone and pyridone compounds, have two or more reaction sites in alkylation reactions. Accordingly, there is no process for producing O-alkylated products of these compounds at a high selectivity or such processes, if any, are applicable exclusively to those having limited structures. A process for selectivity O-alkylating such a compound as described above by converting it into the copper salt by using a monovalent copper compound such as copper suboxide and then reacting it with an alkylating agent having a leaving group in the presence of a phosphorus compound such as a phosphite. Pyrimidyloxy derivatives or pyridyloxy derivatives obtained by this reaction is useful as intermediates of pesticides or drugs.

Growing community of inventors

Niigata, Japan

Mitsuru Takase