Patent GB-1424454-A (GB)
Title: Indoaniline dye sound track production
IPC: G03C7/24
Filed: 1973-01-18
Abstract: 1424454 Aromatic carboxylic acid amides MINNESOTA MINING & MFG CO 18 Jan 1973 [19 Jan 1972] 2649/73 Heading C2C [Also in Division G2] 1 - Hydroxy - 2 - naphtho - [4<SP>1</SP>- (N - ethyl - N- hexadecyl)-sulphamyl]-anilide is prepared by heating to 80-90‹ C. phenyl 1-hydroxy-2- naphthoate and 4-aminobenzensulpho-(N- ethyl-N-hexadecyl)anilide and distilling off the phenol formed under reduced pressure. 4 - Aminobenzensulpho - (N - ethyl - N - hexadecyl)anilide is prepared by refluxing the corresponding nitro compound in acetic acid and dioxane to which is added powdered iron. 4 - Nitrobenzensulpho - (N - ethyl - N - hexadecyl) anilide is prepared by heating 4-nitrobenzensulphonyl chloride, triethylamine, N-ethyl-N- cetylamine and anhydrous dioxane. 1- Hydroxy - 4 - chloro - 2 - naphtho - [4 - (N - ethyl- N - hexadecyl)sulphamyl]- anilide is prepared similarly. 1-Hydroxy-4-chloro-2-naphtho-[4<SP>1</SP>-sulpho - (3<SP>11</SP>,5<SP>11</SP> - dicarbomethoxy) - (N - cetyl) anilido]anilide is prepared from 4-amino benzensulpho[(3<SP>1</SP>,5<SP>1</SP> - dicarbomethoxy) - N- cetyl]-anilide and phenyl 1-hydroxy-4-chloro- 2-naphthoate. 1-Hydroxy-2-naphtho-[4<SP>1</SP>-sulpho- (3<SP>11</SP>,5<SP>11</SP> - dicarbomethoxy) - (N - cetylanilido]- anilide is prepared similarly. 1-Hydroxy-2- naphtho - [4<SP>1</SP> - carboxy - (2 - ethyl)butyl] - anilide is prepared by heating 2-ethylbutyl 4-aminobenzoate and phenyl 1-hydroxy-2-naphthoate and distilling off the phenol formed under vacuum. 2-Ethylbutyl 4-aminobenzoate is prepared by catalytically hydrogenating the corresponding nitro compound using palladium on carbon catalyst. 2-Ethylbutyl 4-nitrobenzoate is prepared by heating at 90‹ C. 4-nitrobenzoyl chloride and 2-ethylbutanol. 1-Hydroxy-4- chloro - 2 - naphtho - (4<SP>1</SP>- carboxydodecyl)anilide is prepared from dodecyl p-aminobenzoate and phenyl 1-hydroxy-4-chloro-2-naphthoate. 2<SP>1</SP>- (1<SP>11</SP> - Hydroxy - 211 - naphthoyl)amino - 4 - tetradecanylamidodiphenyl sulphone is prepared from 2-amino-4<SP>1</SP>-tetradecanylamidodiphenylsulphone and phenyl 1-hydroxy-2-naphthoate. 2 - Amino 4<SP>1 </SP>- tetradecanylamidodiphenylsulphone is prepared by catalytically reducing the corresponding nitro compound. 2-Nitro- 4<SP>1</SP> - tetradecanylamidodiphenylsulphone is prepared by heating sodium 4-tetradecanylamidobenzensulphinate, ethylene glycol, diethylene glycol monoethyl ether and 2- chloronitrobenzene. 1-Hydroxy-2-naphtho-{N- [α - phenyl - # - (4<SP>1</SP>- nonyl) - phenoxy]ethyl}- amide is prepared from 1-phenyl-1-amino-2-(4<SP>1</SP>- nonyl)-phenoxyethane and phenyl 1-hydroxy- 2-naphthoate. 1-Hydroxy-4-chloro-2-naphtho- (N-lauryl)amide is prepared from dodecylamine and phenyl 1-hydroxy-4-chloro-2-naphthoate. 1 - Hydroxy-2-naphtho - [N - (2 - ethyl) - hexyl]- amide is prepared similarly. 1-Hydroxy-2- naphtho - {N - [(2<SP>1</SP>,4<SP>1</SP> - di - tert - amylphenoxy)- butyramido]-ethyl}amide is prepared by refluxing 1-hydroxy-2-naphtho-#-aminoethylamide in acetone and N,N-diethylaniline. 3,4 - Di - (tert - amyl)phenoxybutyroyl chloride is prepared by heating 2,4-di-(tert-amyl)phenoxybutyric acid and thionyl chloride. 1-Hydroxy-4- chloro - 2 - naphtho - {N - [α - phenyl - # - (4<SP>11</SP>- nonyl) - phenoxy] - ethyl}amide is prepared from phenyl 1-hydroxy-4-chloro-2-naphthoate and 1-phenyl-1-amino-2-(4<SP>1</SP>-nonyl)phenoxyethane. 1-Phenyl-1-amino-2-(4<SP>1</SP>-nonyl)-phenoxyethane is prepared by mixing 22% liquid ammonia and 100% formic acid, adjusting the pH to 5-6 by adding formic acid, heating to 180‹ C., adding #-(4<SP>1</SP>-nonyl)phenoxyacetophenone, adding concentrated HCl, refluxing, cooling, redissolving with water after decantation of the liquid phase, dissolving the residue in methanol, adding 30% hydrated sodium, heating and pouring into ice water. #-(4<SP>1</SP>- Nonyl) - phenoxyacetophenone is prepared by refluxing p-nonylphenone, 99% ethanol, KOH and #-bromoacetophenone.