Aromatic diamine, an intermediate therefor, a method for producing the aromatic diamine, and a method for producing the intermediate therefor

A method for preparing a compound represented by the following formula (1-e):

• wherein R1, R2, R3 and R4 are, independently of each other, a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, B is a nitro group or an amino group, and Q is an oxygen atom or a sulfur atom,
• wherein the method comprises a step of reacting a nitrophenyl benzothiazole or nitrophenyl benzoxazole compound represented by the following formula (2):
• wherein Q, R1, R2, R3 and R4 are as defined above and X is a halogen atom,
• with a phenol compound represented by the following formula (3) or a metal salt of said phenol compound:
• wherein B is a nitro group or an amino group,
• to thereby prepare the compound represented by the aforesaid formula (1-e).

A method for preparing a compound represented by the following formula (1-f):

• wherein R1, R2, R3 and R4 are, independently of each other, a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, B is a nitro group or an amino group, and Q is an oxygen atom or a sulfur atom,
• wherein the method comprises a step of reacting an aminophenyl benzothiazole or aminophenyl benzoxazole compound represented by the following formula (4):
• wherein Q, R1, R2, R3 and R4 are as defined above and X is a halogen atom,
• with a phenol compound represented by the following formula (3) or a metal salt of said phenol compound:
• wherein B is a nitro group or an amino group,
• to thereby prepare the compound represented by the aforesaid formula (1-f).

A method for preparing a compound represented by the following formula (1-a):

• wherein R1, R2, R3 and R4 are, independently of each other, a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, and Q is an oxygen atom or a sulfur atom,
• wherein the method comprises a step of reducing a nitro group of a compound represented by the following formula (1-e) or (1-d) to thereby prepare the compound represented by the aforesaid formula (1-a),
• wherein R1, R2, R3 and R4 are, independently of each other, a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, B is a nitro group or an amino group, and Q is an oxygen atom or a sulfur atom,
• wherein R1, R2, R3 and R4 are, independently of each other, a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, and Q is an oxygen atom or a sulfur atom.