Method of producing 2-alkyl-3-aminothiophene derivative
AssigneeMitsui Chemicals Agro, Inc.
InventorsYasuaki Fukazawa, Yoji Aoki, Haruko Mita, Hironori Komatsu
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Abstract
The present invention provides a method of producing 2-alkyl-3-aminothiophene derivative represented by Formula (4), the method comprising oxidizing a compound represented by the following Formula (1) to produce a compound represented by the following Formula (3) and reducing the compound represented by the following Formula (3): wherein in Formula (1), Formula (3), and Formula (4), R represents an alkyl group, a cycloalkyl group, or a bicycloalkyl group; and X represents a hydroxyl group, a halogen atom acyloxy group, an alkylsulfonyl group, or an arylsulfonyl group.
Claims19
A method of producing a 2-alkyl-3-aminothiophene derivative represented by Formula (4), the method comprising (A) oxidizing a compound represented by Formula (1) to produce a compound represented by Formula (3), and (B) reducing the compound represented by Formula (3):
- wherein, in Formula (1), R represents a substituent represented by the following Formula (6):
- wherein, in Formula (6), R1 represents a hydrogen atom, or a straight-chain or branched alkyl group having 1 to 6 carbon atoms and # represents a site of bonding with the compound represented by Formula (1);
- and X represents a hydroxy group, a halogen atom or a substituent represented by the following Formula (2):
- #-O-A(O)n-Q (2)
- wherein, in Formula (2), A represents a carbon atom or a sulfur atom;
- n is 1 when A is a carbon atom, and is 1 or 2 when A is a sulfur atom;
- Q represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a hydrocarbyloxy group having 1 to 10 carbon atoms, or an aryl group that may be substituted by an alkyl group having 1 to 6 carbon atoms;
- and # represents a site of bonding with the compound represented by Formula (1):
- wherein, in Formula (3), R is the same as in Formula (1):
- wherein, in Formula (4), R is the same as in Formula (1).
A 3-nitrotetrahydrothiophene derivative represented by the following Formula (1):
- wherein, in Formula (1), R represents a substituent represented by the following Formula (6):
- wherein, in Formula (6), R1 represents a hydrogen atom, or a straight-chain or branched alkyl group having 1 to 6 carbon atoms and # represents a site of bonding with the 3-nitrotetrahydrothiophene derivative;
- and X represents a hydroxy group, a halogen atom, or a substituent represented by the following Formula (2):
- #-O-A(O)n-Q (2)
- wherein, in Formula (2), A represents a carbon atom or a sulfur atom;
- n is a 1 when A is a carbon atom, and is 1 or 2 when A is a sulfur atom;
- and Q represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a hydrocarbyloxy group having 1 to 10 carbon atoms, or an aryl group that may be substituted by an alkyl group having 1 to 6 carbon atoms.
A 3-nitro-2,5-dihydrothiophene derivative represented by the following Formula (5):
- wherein, in Formula (5), R represents an alkyl group having 1 to 18 carbon atoms that may be substituted by an alkyl group having 1 to 10 carbon atoms or by a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms that may be substituted by an alkyl group having 1 to 10 carbon atoms or by a cycloalkyl group having 3 to 10 carbon atoms, or a bicycloalkyl group having 6 to 12 carbon atoms that may be substituted by an alkyl group having 1 to 10 carbon atoms or by a cycloalkyl group having 3 to 10 carbon atoms.
A 2-alkyl-3-nitrothiophene derivative represented by the following Formula (3):
- wherein, in Formula (3), R represents a substituent represented by the following Formula (6):
- wherein, in Formula (6), R1 represents a hydrogen atom, or a straight-chain or branched alkyl group having 1 to 6 carbon atoms, and # represents a site of bonding with the 2-alkyl-3-nitrothiophene derivative.
Dependencies are inferred from the claim text.