GB857028A - Improvements in or relating to the production of coloured photographic images - Google Patents

Abstract

2- {b -[p-(1; 1; 3; 3-Tetramethyl-butyl) phenoxy] ethoxy}-5-carbethoxymethylcarbamyl-a (p-methyl benzoyl)acetanilide is prepared by reacting p-{-b -[-p-(1; 1; 3; 3-tetramethyl-butyl) phenoxy] ethoxy}-3-amino-benzolylamino acetic acid ethyl ester with p-toluyl acetic acid ethyl ester by refluxing in xylene. The ester may be hydrolysed to give the free acid. The corresponding 5-carbethoxy and 5-(3;5-dicarbethoxyphenylcarbamyl acetanilides are similarly prepared from the corresponding 3-amino-benzoic acid ethyl ester or substituted amide. The 3-amino-benzoic acid ethyl ester also may be reacted with p-anisoyl acetic acid ethyl ester to give the 2-substituted-5-carbethoxy-a -(p-methoxybenzoyl) acetanilide. The products may be similarly hydrolysed to the free acids.2- {b -[p-(1;1;3;3-tetramethylbutyl)phenoxy] ethoxy}-5-p-sulphophenylcarbamyl - benzoyl-acetanilide is similarly prepared by reacting p-{b -p-(1; 1; 3; 3-tetramethyl-butyl) phenoxy] ethoxy-3-amino-N-(p-fluoro-sulphophenyl) - benzamide with benzoyl acetic acid ethyl ester and hydrolysing the fluorosulpho group to the free sulphonic acid. 2-Cetoxy-5-carbomethoxy-a (p-methylbenzoyl) acetanilide is similarly prepared from 4-cetoxy-3-amino-benzoic acid methyl ester and p-toldyl acetic acid ethyl ester. The product may be hydrolysed to the free acid. 4-{b -[p-(1; 1; 3; 3-tetramethyl-butyl) phenoxy] ethoxy}-3-amino-benzoylamino acetic acid ethyl ester is prepared by reduction of the 3-nitro compound with iron and acetic acid. The corresponding 4-substituted-3-nitrobenzoic acid ethyl ester and 4-substituted-3-nitro-N-(3; 5-dicarbomethoxy-phenyl)-benzamide are similarly reduced to the 3-amines. 4-{b -[p-(1; 1; 3; 3-tetramethyl-butyl) phenoxy] ethoxy}-3-amino-N-(p-fluorosulphophenyl)-benzamide and 4-cetoxy-3-amino-benzoic acid methyl ester are similarly prepared from the 3-nitro compounds. 4-{b -[p-(1; 1; 3; 3-tetramethyl-butyl) phenoxy] ethoxy}-3-nitro-benzoic acid methyl ester is prepared by boiling 3-nitro-4-hydroxy-benzoic acid methyl ester with the tolusulphonate of b -[p-(1; 1; 3; 3-tetramethyl-butyl) phenoxy] ethanol in a solvent. The corresponding ethyl ester is similarly prepared. The methyl ester is hydrolysed to the acid which is reacted with thionyl chloride to give the corresponding acid chloride. This in turn is reacted with amines NH2R, where R is -CH2CO2C2H5, 3; 5-dicarbo-methoxyphenyl or p-fluorosulphophenyl to give 4-{b -[p-(1; 1; 3; 3-tetramethyl-butyl) phenoxy] ethoxy}-3-nitro-N-substituted-benzamides. 4-Cetoxy-3-nitro-benzoic acid methyl ester is prepared by adding cetyl tolusulphonate to a boiling alkaline solution of methyl-3-nitro-4-hydroxy-benzoate. Specifications 458,664, 531,246 774,421, 808,276 and U.S.A. Specification 2,184,303 are referred to.