Patent GB-595314-A (GB)
Title: Improvements in photographic colour forming developers and process of colour development
IPC: G03C7/36
Filed: 1944-11-02
Abstract: N - (3 - (o1 - Anisoylbenzoylacet) - amino - 4 - chlorobenzenesulphonyl) - N - (g  - phenyl - n - propyl) - p - toluidide is prepared by adding N - (3 - amino - 4 - chlorobenzenesulphonyl) - N - (g  - phenyl - n - propyl) - p - toluidide to a heated mixture of ethyl o - methoxybenzoylacetate and bromobenzene.  O-Anisoylacetanilide, 2 - methoxy - 5 - methylbenzylacetanilide, N - 2 - methoxybenzoylaceto - N1 - a  - (41 - butylphenoxy) - propionyl - p - phenylenediamine, N - 2 - methoxybenzoylaceto - N 1 - a  - (41 - butylphenoxy) - propionyl - m - phenylenediamine, N - 2 - n - propoxybenzoylaceto - N1 - a  - (41 - butylphenoxy) - propionyl - p - phenylenediamine, N - 2 - methoxybenzoylaceto - N - a  - (41 - amylphenoxy) - n - butyryl - p - phenylenediamine, N - 2 - methoxybenzoylaceto - N1 - a  - (41 - amylphenoxy)-propionyl - p - phenylenediamine, N - ((4 - o - anisoylacet) - aminobenzenesulphonyl) - N - (g  - phenyl - n - propyl) - p - toluidide, o - anisoylacet - o1 - chloranilide, 2 - methoxy - 5 - methyl benzoylacet-o-chloranilide, N-(4-(o-anisoylacet)-anino - 31 - chlorobenzenesulphonyl) - N - methyl-p - toludine, 1 - (o - anisoylacet) - amino - 2 - chloro - 4 - (a  - (p - butylphenoxy) - propionyl - aminobenzene, N - (4 - (o - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - N - methyl - p - chloranilide, N - (4 - (o1 - anisoylacet) - amino - 3-chlorobenzenesulphonyl) - N - methylanilide, N-(4 - (o1 - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - p - toluidide, N - (4 - (o1 - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - p - phenylaniline, N - (4 - (o1 - anisoylacet) - amino-3 - chlorobenzenesulphonyl) - p - tert. - amylanilide, 1 - (o - anisoylacet) - amino - 2 - chloro - 4 - (p1 - toluenesulphonyl) - aminobenzene, N-(4-(o1 - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - N - (g  - phenyl - n - propyl - p - toluidide and 21 - methoxybenzoylacet - 2 - chloro - 4 - nitranilide are similarly prepared.  N - 4 - (o1 - Anisoylchloracet) - amino - 3 - chlorobenzenesulphonyl) - N - (g  - phenyl - n - propyl) - p - toluidide is prepared by chlorinating N - 4 - (o1 - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - N - (g  - phenyl - n - propyl)-p-toluidide in chloroform solution with sulphuryl chloride. 1 - (o - Anisoylacet) - amino - 2 - chloro - 4 - acetylthioglycollylaminobenzene is prepared by condensing 4-(21-methoxybenzoylacetamino)-3-chloraniline with acetylthioglycollyl chloride in the presence of sodium acetate or quinoline.  Ethyl 2-methoxy-5-methylbenzoylacetate is prepared by reacting ethyl malonyl chloride and p-methoxytoluene in benzene in the presence of anhydrous aluminium chloride.  Ethyl o-propoxybenzoylacetate is prepared from methyl o-n-propoxybenzoate and ethyl acetate in the presence of sodium.  Acetylthioglycollyl chloride is prepared by reacting acetylthioglycollic acid with thionyl chloride.  4 - (a  - (41 - tert. - Butylphenoxy) - n - propionamido) - aniline is prepared by reducing N - (a  - (41 - tert. - butylphenoxy) - n - propionyl) - 4 - nitraniline in ethyl alcohol with hydrogen in presence of Raney nickel. 3-(a -(41 - tert. - Butylphenoxy) - n - propionamide) - aniline, 4 - (a  - (41 - tert. - amylphenoxy) - butyramido) - aniline, 4 - (a  - (41 - tert. - amylphenoxy)-propionamido) - aniline, 4 - (a  - (41 - tert. - butylphenoxy) - propionamido) - 2 - chloraniline, 4-(21 - methoxybenzoylacetamino) - 3 - chloraniline hydrochloride, and N-(3-amino-4-chlorobenzenesulphonyl) - N - g  - phenyl - n - propyl - p - toluidide are similarly prepared.  41 - Amino - 31 - chloro - p - toluenesulphonanilide is prepared by refluxing together 41-acetamido - 31 - p - toluenesulphonanilide, concentrated hydrochloric acid, and ethyl alcohol, and pouring into aqueous caustic alkali.  4 - Amino - 3 - chlorobenzenesulphonmethyl-3 - chlorobenzenesulphonmethyl - p1 -chloroanilide, 4 - amino - 3 - chlorobenzenesulphonmethyl - 41 - toluidide, 4 - amino - 3 - chlorobenzenesulphon - p1 - toluidide, N - (4 - amino - 3 - chlorobenzenesulphon) - 41 - tert. - amylanilide, N - (41 - amino-3 - chlorobenzenesulphon) - N - g  - phenylpropyl - p1-toluidide, and N-(p-aminobenzenesulphon)-N - g  - phenyl - n - propyl - p - toluidide are similarly prepared.  N - (a  - (41 - tert. - Butylphenoxy) - n - propionyl) - 4 - nitraniline is prepared by reacting together p-nitraniline, and a -(p-tert.-butylphenoxy)-n-propionyl chloride in the presence of acetic acid and anhydrous sodium acetate.  N - (a  - (41 - tert. - Butylphenoxy) - n - propionyl) - 3 - nitraniline, N - (a  - (41 - tert. - amylphenoxy) - n - butyryl) - 4 - nitraniline, N - (a  - (41 - tert. - amylphenoxy) - n - propionyl) - 4 - nitraniline, N - (a  - (41 - tert. - butylphenoxy)-n-propionyl) - 3 - chloro - 4 - nitraniline, and N - (4 - chloro - 3 - nitrobenzenesulphonyl) - N - a - phenyl - n - propyl - p - toluidide are similarly prepared.  41 - Acetamino - 31 - chloro - p - toluenesulphonanilide is prepared by heating together 4-acetamino-3-chloroaniline and p-toluenesulphonyl chloride in presence of acetic acid and anhdrous sodium acetate. 4-Acetamino-3-chlorobenzenesulphonmethylanilide, 4 - (41 - acetamino - 31 - chlorobenzenesulphonamide) - diphenyl, 41 - acetamino - 31 - chlorobenzenesulphomethyl - 4 - chloranilide, 41 - acetamino - 31 - chlorobenzenesulphonmethyl - 4 - toluidide, 4 - (41 - acetamino-31 - chlorobenzenesulphon) - toluidide, N - (41 - acetamino - 31 - chlorobenzenesulphon) - 4 - tert.-amylanilide, N - (41 - acetamino - 31 - chlorobenzenesulphonyl) - N - g  - phenylpropyl - p - toluidide and N - (p - acetaminobenzenesulphon)-N - g  - phenyl - n - propyl - p - toluidide are similarly prepared.  Specifications 427,472, 427,516, 427,518, 427,520, 440,032, 440,089, 447,092, 507,841, 524,154, 524,555, 540,366, 540,368, 541,589, and 545,448, [all in Group XX], are referred to.