Patent GB-791219-A (GB)
Title: Method of making dispersions of colour couplers for use in light-sensitive silver salt emulsions
IPC: G03C7/388
Filed: 1955-11-09
Abstract: 2 - (a  - Di - tert. - amylphenoxy - n - butyrylamino) - 4:6 - dichloro - 5 - methylphenol is prepared by reacting 2-amino-4,6-dichloro-5-methylphenol hydrochloride with a -di-tert.-amylphenoxy-n-butyryl chloride in acetone containing quinoline.  2 - Amino - 4:6 - dichloro - 5 - methylphenol hydrochloride is prepared by reacting 2-amino-4-chloro-5-methylphenol with glacial acetic acid and acetic anhydride to form the acetyl derivative, reacting with sulphuryl chloride, and boiling ethyl alcohol and hydrochloric acid.  a  - Di - tert. - amylphenoxy - n - butyryl chloride is prepared by reacting with thionyl chloride a  - di - tert. - amylphenoxy - n - butyric acid, itself prepared by reacting di-tert.-amyl phenol with a -bromo-n-butyric acid.  6 - {4 - [a  - 2:4 - Di - tert. - amylphenoxy)-butyramido] - phenoxyacetamido} - 2:4 - dichloro-3-methylphenol is prepared b refluxing together 6 - (4 - aminophenoxyacetamido)-2:4 - dichloro - 3 - methylphenol and a - (2:4-di - tert. - amylphenoxy) - n - butyryl chloride with acetone containing dimethylaniline.  6 - (4 - Aminophenoxyacetamido) - 2:4 - dichloro - 3 - methylphenol is prepared by reducing with hydrogen in the presence of nickel and pyridine 6-(4-nitrophenoxyacetamido)-2:4-dichloro-3-methylphenol, itself prepared by refluxing together 2 - amino - 4:6 - dichloro - 5-methylphenol hydrochloride and p - nitrophenoxyacetyl chloride in acetone containing dimethylaniline.  p-Nitrophenoxyacetyl chloride is prepared by refluxing with thionyl chloride p-nitrophenoxyacetic acid, itself prepared by reacting p-nitrophenol with chloracetic acid in presence of sodium hydroxide.  4 - Chloro - 2 - {3-[a  - 2:4 - di - tert. - amylphenoxy) - acetamido] - benzamido} - 5 - methylphenol is prepared by reacting with a -(2:4-di-tert.-amylphenoxy)-acetyl chloride in acetone containing N:N - dimethylaniline 2 - (3-aminobenzamido) - 4 - chloro - 5 - methylphenol, itself prepared by reducing with iron and acetic acid 2 - (3 - nitrobenzamido) - 4 - chloro - 5 - methylphenol, prepared by reacting 2-amino-4-chloro - 5 - methylphenol with m - nitrobenzoyl chloride in acetone containing dimethylaniline.  a  - (2:4 - Di - tert. - amylphenoxy) - acetyl chloride is prepared by reacting with thionyl chloride 2:4 - di - tert. - amylphenoxyacetic acid, itself prepared by reacting 2 : 4-di-tert.-amylphenol with chloracetic acid in the presence of sodium hydroxide.  a  - {3 - [2 : 4 - Di - tert. - amylphenoxyacetamido] - benzoyl} - 2 - methoxyacetanilide is prepared by reacting with 2 : 4-di-tert.-amylphenoxyacetyl chloride in the presence of acetic acid and anhydrous sodium acetate a -(m - aminobenzoyl) - 2 - methoxyacetanilide hydrochloride, itself prepared by reducing with iron and hydrochloric acid a -(m-nitrobenzoyl)-2-methoxyacetanilide, prepared by refluxing ethyl a  - (m - nitrobenzoyl) - acetate with o-anisidine in xylene.  3 - Benzoylacetamido - 4 - methoxy - (21 : 41-di - tert. - amylphenoxy) - acetanilide is prepared by reacting with 2 : 4-tert.-amylphenoxyacetyl chloride in the presence of acetic acid and anhydrous sodium acetate a -benzoyl-5-amino-2-methoxyacetanilide, prepared by reducing with hydrogen in presence of Raney nickel a -benzoyl - 2 - methoxy - 5 - nitroacetanilide, prepared by refluxing 4 - nitro - 2 - aminoanisole with ethyl benzoylacetate in xylene.  4 - Benzoylacetamido - 3 - methoxy - (21 : 41-di - tert. - amylphenoxy) - acetanilide is prepared by reacting with 2 : 4-di-tert.-amylphenoxyacetyl chloride in the presence of acetic acid and anhydrous sodium acetate a -benzoyl-4-amino - 2 - methoxyacetanilide - hydrochloride, prepared by reducing with iron and acetic acid a  - benzoyl - 2 - methoxy - 4 - nitroacetanilide, prepared by refluxing together 2-methoxy-4-nitroaniline and ethyl benzoylacetate in xylene. Specifications 541,589, 545,448, [both in Group XX], 627,814, 649,660, 680,488, 736,922 and 739,913 are referred to.ALSO:1 - (21 : 41 : 61 - Trichlorophenyl) - 3 - (311-(2111 : 4111 - di - tert. - amylphenoxyacetamido) - benzamido) - 4 - (p - methoxyphenylazo) - 5 - pyrazolone is prepared by reacting with diazotized p-anisidine 1-(21 : 41 : 61-trichlorophenyl)-3 - (311 - (2111 : 4111 - di - tert. - amylphenoxyacet - amido) - benzamido - 5 - pyrazolone. Specifications 541,589, 545,448, [both in Group XX], 627,814, 649,660, 680,488, [all in Group IV (b)], 736,922 and 739,913 are referred to.