Schwefelsaeureestergruppen enthaltende Acylacetylaminoverbindungen und Verfahren zu deren Herstellung

摘要

The invention relates to compounds of the formula in which R1 is a benzene residue, R2 is a benzene, cycloalkyl or alkyl residue, R3 is an alkyl residue containing at least 3 carbon atoms and Y is an acid sulphuric acid ester group, which may be in acid or salt form. The benzene residue(s) may be further substituted, e.g. with halogen atoms or methyl or ethyl groups or methoxy or ethoxy groups. The compounds are obtained by reacting chlorosulphonic acid in an organic solvent with a compound of the formula in which R1, R2 and R3 are as above and X is a methoxy or ethoxy group. A number of solvents are specified. Compounds of Formula II above may themselves be obtained by condensing amines of the formula with esters of the formula in which A is a methyl or ethyl group. Examples are given in which (1) 1-amino-2-stearoyl-amino-5-methoxybenzene is condensed with p-methoxybenzoyl-acetic acid ethyl ester and the product is reacted with chlorosulphonic acid in methylene chloride to yield a product of the formula (2) products of the formulae are similarly obtained. The products are useful in photography (see Division G2). The preparation of some starting materials and intermediates used in the process is described, as follows: A stearoylaminohexahydrobenzoylaminomethoxybenzene is prepared by condensing 1-amino-2-stearoyl-amino-5-methoxybenzen with hexahydrobenzoylacetic acid ethyl ester. A stearoylaminobenzoylaminoethoxybenzene is prepared similarly from 1-amino-2-stearoyl-amino-5-ethoxybenzene and benzoylacetic acid ethyl ester. A stearoylaminobenzoylaminomethoxybenzene is prepared similarly from 1-amino-4-stearoyl-amino-5-methoxybenzene and benzoylacetic acid ethyl ester. A stearoylamino - p - methylbenzoylamino-methoxybenzene is prepared similarly from 1-amino-2-stearoylamino-5-methoxybenzen and p-methylbenzoylacetic acid ethyl ester. A lauroylaminobenzoylaminomethoxybenzene is prepared similarly from 1-amino-2-lauroyl-amino-5-methoxybenzene and benzoylacetic acid methyl ester. 1 - Stearoylamino - 4 - ethoxybenzene is prepared from 1 - amino - 4 - ethoxybenzene and stearic acid. 1 - Stearoylamino - 4 - ethoxy - 2 - nitrobenzene is prepared by nitrating 1-stearoylamino-4-ethoxybenzene. 1 - Stearoylamino - 4 - ethoxy - 2 - amino-benzene is prepared by catalytic hydrogenation of the 2-nitro compound. 5 - Nitro - 2 - stearoylamino - 1 - methoxy-benzene is prepared from 5-nitro-2-amino-1-methoxybenzene and stearoyl chloride. 5 - Amino - 2 - stearoylamino - 1 - methoxy benzene is prepared by catalytic hydrogenation of the 5-nitro compound. 4 - Lauroylamino - 3 - nitro - 1 - methoxy benzene is prepared from 4-amino-3-nitro-1-methoxybenzene and lauroyl chloride. 4 - Lauroylamino - 3 - amino - 1 - methoxy-benzene is prepared by catalytic hydrogenation of the 3-nitro compound.