Patent GB-990627-A (GB)
Title: Method of preparing non-migratory colour couplers for yellow
IPC: G03C7/36
Filed: 1961-05-08
Abstract: Compounds of the formula R-CO-CH2-CO-NH-Ar(SO3Me)ZD wherein R is a methyl radical, an aryl or substituted aryl radical, or a heterocyclic radical, Ar is a nucleus of the benzene series, Me is hydrogen, an alkali metal or ammonium, Z is oxygen, sulphur, a sulphonyl group or an >N(alkyl) group, and D is an aliphatic radical of 5-20 carbon atoms, are prepared by condensing diketene or a compound of the formula R1-CO-CH2-CO-OR2 where R1 is an aryl or substituted aryl ardical or a heterocyclic radical and R2 is a lower alkyl radical, with an amine of the formula H2NAr(SO2F)ZD wherein Ar, Z and D are as above; the sulphofluoride group in the products may then be saponified.  In the examples: (1) 2-cetylmercapto - 5 - fluorosulphonylaniline (c.f. Specification 983,648) and a -furoylacetic acid ethyl ester yield a -furoyl-(2-cetylmercapto-5-fluorosulphonyl) - acetanilide, which may be saponified to yield a  - furoyl - (2 - cetylmercapto - 5-sulpho) - acetanilide (2) 2 - cetylsulphonyl - 5-fluorosulphonyl - aniline (cf. German Specification 1,109,522) and a  - furoylacetic acid ethyl ester yield a -furoyl-(2-cetylsulphonyl-5-fluorosulphonyl) - acetanilide, which may be saponified to yield a -furoyl-(2-cetylsulphonyl-5 - sulpho) - acetanilide; (3) 3 - fluorosulphonyl - 4 - cetylmercaptoanilino (cf. Specification 983,648) and isonicotinoylacetic acid ethyl ester yield isonicotinoyl - (3 - fluorosulphonyl - 4 - cetylmercapto) - acetanilide, which may be saponified to yield isonicotinoyl-(3-sulpho - 4 - cetylmercapto) - acetanilide; (4) 2-cetylmercapto - 5 - fluorosulphonyl - aniline and p-methoxybenzoylacetic acid ethyl ester yield p - methoxybenzoyl - (2 - cetylmercapto - 5-fluorosulphonyl) - acetanilide, which may be saponified to yield p-methoxybenzoyl-(2-cetylmercapto - 5 - sulpho) - acetanilide; (5) 2-cetylmercapto - 5 - fluorosulphonyl - aniline and benzoylacetic acid ethyl ester yield benzoyl-(2 - cetylmercapto - 5 - fluorosulphonyl)-acetanilide, which may be saponified to yield benzoyl - (2 - cetylmercapto - 5 - sulpho) - acetanilide; (6) 2 - cetylsulphonyl - 5 - fluorosulphonyl - aniline and diketene yield acetyl - (2-cetylsulphonyl - 5 - fluorosulphonyl) - acetanilide, which may be saponified to yield acetyl-(2 - cetylsulphonyl - 5 - sulpho) - acetanilide; (7) 2 - cetylsulphonyl - 5 - fluorosulphonylaniline and benzoylacetic acid ethyl ester yield benzoyl - (2 - cetylsulphonyl - 5 - fluorosulphonyl)-acetanilide, which may be saponified to yield benzoyl - (2 - cetylsulphonyl - 5-sulpho) - acetanilide; (8) 2 - cetyloxy - 5-fluorosulphonyl - aniline (cf. Specification 983,648) and benzoylacetic acid ethyl ester yield benzoyl - (2 - cetyloxy - 5 - fluorosulphonyl)-acetanilide, which may be saponified to yield benzoyl - (2 - cetyloxy - 5 - sulpho)-acetanilide; (9) 2 - (N - methylcetyl) amino-5 - fluorosulphonyl - aniline (cf. Belgian Specification 590,934) and benzoylacetic acid ethyl ester yield benzoyl-[2-(N-methylcetyl) amino - 5 - fluorosulphonyl] - acetanilide, which may be saponified to yield benzoyl-[2-(N - methylcetyl) amino - 5 - sulpho] - acetanilide; (10) 3 - fluorosulphonyl - 4 - cetylmercaptoaniline and benzoylacetic acid ethyl ester yield 3-fluorosulphonyl-4-cetylmercapto-acetanilide, which may be saponified to yield benzoyl - (3 - sulpho - 4 - cetylmercapto) - acetanilide; (11) 2 - cetylmercapto - 5 - fluorosulphonyl - aniline and a  - thienoylacetic acid ethyl ester yield a -thienoyl-(2-cetylmercapto-5-fluorosulphonyl)-acetanilide, which may be saponified to a -thienoyl-(2-cetylmercapto-5-sulpho) - acetanilide; (12) 2 - cetylmercapto - 5-fluorosulphonylaniline and mesitoylacetic acid ethyl ester yield mesitoyl - (2 - cetylmercapto-5 - fluorosulphonyl) - acetanilide, which may be saponified to yield mesitoyl-(2-cetylmercapto - 5 - sulpho) - acetanilide.  The saponified products are useful in colour photography as non-migratory couplers for yellow.  Specification 808,276 also is referred to.