GB595844A - Improvements in and relating to the production and processing of photographic materials - Google Patents

Abstract

Thioglycollic and acetylthioglycollic amides are prepared by reacting thioglycollic acid or acetylthioglycollic chloride with the appropriate amine. 2-Hydroxy-3 : 5-dichloro-4-methylthioglycollic anilide is prepared by heating 2-amino-4 : 6 - dichloro - 5 - methylphenol hydrochloride with thioglycollic acid and quinoline. 2-Hydroxy-thioglycollic anilide, 2 - hydroxy - 4 - methylthio - glycollic anilide, 2-hydroxy-4-methoxythioglycollic anilide, 2 -hydroxy-4-methyl-5-chlorothioglycollic anilide, 5 - (thioglycollylamino) - 1 - naphthol, and 1-phenyl-3-(thioglycollylamino)-5-pyrazolone are similarly prepared. 2-Hydroxy-4-methyl-5-chloro-a -dimethylthioglycollic anilide is similarly prepared using the free base of the corresponding amine, no quinoline, and a -mercaptoisobutyric acid. p-Acetylthioglycollylamino-o -cyanacetophenone is prepared by adding quinoline and then acetylthioglycollic chloride to a solution of p-amino-o -cyanacetophenone in dioxane. o -Benzoylacetamino - p - acetylthio - glycollic and o -benzoylacetamino-m-thioglucollic anilides are similarly prepared, and o -benzoylacetamino - p - thioglycollic and o - benzoylacetamino-m-thioglycollic anilides are prepared by hydrolysing the last-mentioned compounds with aqueous sodium hydroxide. Acetoacetylamino-p-acetylthioglycollic anilide is prepared by condensing p-(acetacetamino)-aniline with acetylthioglycollylchloride. 2 - a - Acetylmercaptopropionamido)-4 : 6-dichloro-5-methylphenol is prepared by reacting 2-(a -bromopropionamido)-4 : 6-dichloro-5-methylphenol with potassium thioacetate. Acetylthioglycollic acid is prepared by acetylating thioglycollic acid with acetyl chloride. Acetylthioglycollic chloride is prepared by reacting acetylthioglycollic acid with thionyl chloride. 2 - (a - Bromopropionamido) - 4 : 6 - dichloro - 5 - methylphenol is prepared by adding a -bromopropionyl bromide to a suspension of 2-amino-4 : 6-dichloro-5-methylphenol hydrochloride and anhydrous sodium acetate in glacial acetic acid. 2-Amino-4 : 6-dichloro-5-methylphenol hydrochloride is prepared by acetylating 2-amino-4-chloro-5-methylphenol with acetic acid and acetic anhydride, chlorinating with sulphuryl chloride, and hydrolysing by boiling with hydrochloric acid. p-Amino-o -cyanoacetophenone is prepared by hydrolysing p - cyanoacetylacetanilide in alcoholic solution by boiling with hydrochloric acid. p-Cyanoacetyl-acetanilide is prepared by heating p-chloroacetyl-acetanilide with an aqueousethyl alcohol solution of sodium cyanide. m-(Benzoylacetamino)-aniline is prepared by reducing o - benzoyl - m - nitroacetanilide with hydrogen in the presence of "Raney" nickel. o -(Benzoyl-m-nitroacetanilide is prepared by reacting ethyl benzoylacetate with m-nitraniline. o -Benzoyl-p-nitroacetanilide is similarly prepared. p-(Benzoylacetamino)-aniline hydrochloride is prepared by reducing o -benzoyl-p-nitroacetanilide with zinc and acetic acid, and treating with HCl.