# US 8,785,654 B2 · 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

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- Number: US 8,785,654 B2
- Document ID: US8785654B2
- Status: Granted
- Kind: B2
- Application number: 13/363,091
- Filed: 2012-01-31
- Published: 2012-05-24
- Granted: 2014-07-22
- Earliest claimed: 2007-04-19
- Assignees: Nippon Soda Co., Ltd.
- Applicants: Mitsuru Takase; Fuminori Komatsu
- Inventors: Mitsuru Takase; Fuminori Komatsu
- Web page: https://patentgrep.com/patent/US8785654B2

## CPC

- C07D 233/90: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07C 257/06: having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
- C07C 257/12: having carbon atoms of amidino groups bound to hydrogen atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

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.

## Claims

### Claim 1

A method for producing aminoimidazole derivatives represented by formula (3-V), comprising the steps of carrying out step (C) of cyclizing a compound represented by formula (3-IV) and/or a salt thereof in the presence of a basic aqueous solution, in the presence of an aprotic organic solvent:
in formula (3-IV), each of R1 and R3 is independently a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group,
in formula (3-V), R1 and R3 represent the same meanings as defined in formula (3-IV); and R4 is —CN or —CONH2.

### Claim 2

A method for producing aminoimidazole derivatives represented by the following formula (3-VIII) comprising the steps of carrying out all of
step (A) of reacting diaminomaleonitrile and a compound represented by formula (3-I) in the presence of a strong acid to obtain a compound represented by formula (3-II),
CR31(OR32)3 (3-II)
in formula (3-I), R31 is a hydrogen atom; and each R32 is independently an optionally substituted alkyl group, or an optionally substituted aryl group,
in formula (3-II), R31 and R32 represent the same meanings as defined in formula (3-1),
step (B) of reacting a compound represented by formula (3-II) and a compound represented by formula (3-III) to obtain a compound represented by formula (3-IV) and/or a salt thereof,
R3NH2 (3-III)
in formula (3-III), R3 is a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group,
in formula (3-VI), R31 represents the same meanings as defined in formula (3-I); and R3 represents the same meanings as defined in formula (3-III),
and step (C) of cyclizing a compound represented by formula (3-VI) and/or a salt thereof in the presence of a basic aqueous solution,
in the presence of an aprotic organic solvent,
in formula (3-VIII), R31 represents the same meanings as defined in formula (3-I); R3 represents the same meanings as defined in formula (3-III); and R4 is —CN or —CONH2.

### Claim 3 (depends on 2)

The method for producing aminoimidazole derivatives according to claim 2, wherein the strong acid is trifluoroacetic acid, methanesulfonic acid, p-toluenesulfonic acid, or condensed sulfuric acid.

### Claim 4 (depends on 2)

The method for producing aminoimidazole derivatives according to claim 2, wherein step (B) is carried out by mixing a solution or suspension of the aforementioned compound represented by formula (3-II) in an aprotic organic solvent and an aqueous solution of the compound represented by formula (3-III).

### Claim 5 (depends on 1)

The method for producing aminoimidazole derivatives according to claim 1, wherein the aforementioned aprotic organic solvent is tetrahydrofuran.