Patent ID: 6320078
Filing Date: 2001-11-20
Classification: C07C,C07D

Abstract:
A process for preparing a selectively monoacylated phenylenediamine derivative which comprises the steps of converting, into a benzoylimidazole derivative, a benzoic acid derivative represented by the formula (1) ##STR22##wherein R.sup.1 and R.sup.2 are each independently a hydrogen atom, or a substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acyl group having 1 to 4 carbon atoms, an acylamino group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, a perfluoroalkyloxy group having 1 to 4 carbon atoms and an alkoxycarbonyl group having 1 to 4 carbon atoms, which substituent is located at an optional position on the benzene ring; and R.sup.3 is a hydrogen atom or a substituent which is located at the other optional position than R.sup.1 and R.sup.2 and is represented by the formula (2)A--X--Q--(CH.sub.2).sub.n -- (2)wherein A is a phenyl group or a heterocyclic ring which may be substituted by 1 to 4 groups selected from the group consisting of a halogen atom, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acyl group having 1 to 4 carbon atoms, an acylamino group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, a perfluoroalkyloxy group having 1 to 4 carbon atoms or an alkoxycarbonyl group having 1 to 4 carbon atoms, a phenyl group and a heterocyclic ring; X is a direct bond or one of structures represented by the formulae (3-1) to (3-7): ##STR23##wherein e is an integer of 1 to 4; m is an integer of 0 to 4; R.sup.4 is an alkyl group having 1 to 4 carbon atoms which may be substituted or an acyl group represented by the formula (4) ##STR24##whereinR.sup.6 an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, a phenyl group or a heterocyclic ring which may be substituted;R.sup.5 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be substituted;Q is a substituent represented by one of the formulae (5-1) to (5-9) ##STR25##wherein R.sup.7 is an alkyl group having 1 to 4 carbon atoms which may be substituted, or an acyl group represented by the formula (6) ##STR26##whereinR.sup.6 is as defined above;R.sup.8 and R.sup.9 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be substituted;and n is an integer of 0 to 4,and then reacting the benzoylimidazole derivative with a phenylenediamine derivative represented by the formula (7) ##STR27##wherein R.sup.10 is a hydrogen atom, or a halogen atom, a hydroxyl group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acyl group having 1 to 4 carbon atoms, an acylamino group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, a perfluoroalkyloxy group having 1 to 4 carbon atoms or an alkoxycarbonyl group having 1 to 4 carbon atoms which can substitute at an optional position on a benzene ring, and one of the amino groups can substitute at a remaining optional position on the benzene ring.