Patent GB-1465184-A (GB)
Title: Photographic silver halide elements useful in colour diffusion  transfer processes and chemical compounds useful in said  elements
IPC: G03C8/18
Filed: 1974-02-12
Abstract: 1465184 Magenta azo dye-releasing azo compounds EASTMAN KODAK CO 12 Feb 1974 [12 Feb 1973] 06249/74 Heading C4P [Also in Divisions C2 and G2] Novel compounds have the formulae wherein Car is a carrier moiety comprising a ballast group of a molecular size and configuration such that the compound is non-diffusible in a photosensitive element in the presence of an alkaline aqueous photographic processing composition; X is -R<SP>2</SP>-L n -R<SP>2</SP> p - wherein each R<SP>2</SP> is independently C 1-8  alkylene or optionally substituted C 6-9  phenylene; L is -O-, -CO-, -NHCO-, -SO 2 NH-, -CONH-, -NHSO 2 -, -SO- or -SO 2 -; n is zero or 1; p is 1 when n is 1 and is zero or 1 when n is zero and when p is 1 the total number of C atoms in the R<SP>2</SP> radicals is at most 14; R is H or C 1-6  alkyl; J is -SO 2 - or -CO-; m and q are each zero or 1; Q is H, OH, -NHCOR<SP>3</SP> or -NHSO 2 R<SP>3</SP> wherein R<SP>3</SP> is optionally substituted C 1-6  alkyl, benzyl or optionally substituted C 6-9  phenyl; G is OH, salified OH, OCOR<SP>4</SP> or OCOOR<SP>4</SP> wherein R<SP>4</SP> is C 1-18  alkyl or optionally substituted C 6-18  phenyl; Z is one or more substituents selected from CN, Chal 3 , CO 2 H and salts and esters thereof, C 1-8  alkylsulphonyl, -SO 2 NR<SP>5</SP>R<SP>6</SP> (wherein R<SP>5</SP> is H, optionally substituted C 1-8  alkyl or optionally substituted C 6-13  aryl and R<SP>6</SP> is R<SP>5</SP>, C 2-8  alkyl-, aralkyl- or aryl-carbonyl or alkyl-, aralkyl- or aryl-sulphonyl or R<SP>5</SP> and R<SP>6</SP> together are 1-(dialkylamino)alkylidene containing 1-8 C in each alkyl and 1-4 C in alkylidene), CON(R<SP>5</SP>) 2  wherein each R<SP>5</SP> is the same or different, SO 3 H and salts thereof -SO 2 Na, halogen and Car-[X-(NR-J) q ] m -, R<SP>1</SP> is H, C 1-8  alkoxy, C 1-8  optionally substituted alkyl or the C atoms necessary to form a fusedon benzene ring; E, in the 5-, 6- or 7-position relative to G, is -CON(R<SP>5</SP>) 2 , -SO 2 NR<SP>5</SP>R<SP>6</SP>, free, salified or esterified CO 2 H or free or salified SO 3 H, or E is H; Z<SP>1</SP> is H or Z; and at most one sulpho or carboxy radical or salt thereof is present in each compound. Examples typical of their preparation are as follows (i) 4-amino-N- [4 - (2,4 - di - tert - pentylphenoxy)butyl] - 1- hydroxy - 2 - naphthamide is condensed with 4 - acetamido - 8 - [4 - N - (dimethylaminomethylene)sulphamoylphenylazo] - 5 - hydroxy- 1 - naphthalene sulphonyl chloride to give a compound of the formula i.e. a compound of Formula (I) wherein m is zero and Car constitutes the amino radical from the first named reactant plus SO 2 ; (ii) the compound of the formula i.e. a compound of Formula (I) containing 2 Car moieties, is prepared similarly; (iii) 4-maminobenzenesulphonamido - N - [4 - (2,4 - ditert - pentylphenoxy)butyl] - 1 - hydroxy - 2- naphthamide in CF 3 CO 2 H under N 2  in an icemethanol bath is added to an aqueous NaNO 2  solution and the resulting diazonium salt in solution is coupled with 1,8-dihydroxynaphthalene to give a compound of the formula i.e. a compound of Formula (III) wherein m is zero (compounds wherein m is 1 are prepared similarly); (iv) 4 - (m - aminophenylsulphonamido) - N - [4 - (2,4 - di - tert - pentylphenoxy) butyl] - 1 - hydroxy - 2- -naphthamide is diazotized and coupled with 5-p-toluenesulphonamido-1-naphthol to give a compound of the formula i.e. a compound of Formula (III) wherein m is zero; and (v) sulphanilic acid is diazotized and coupled with an appropriately 5-substituted naphthol to give a compound of the formula i.e. a compound of the Formula (II). In other examples different diazotization and coupling conditions are used, e.g. in one the amine is treated with isopentyl nitrite in THF and the product added to a solution of the coupling component in acetic and propionic acids followed by a little pyridine, and another is similar except that the pyridine is omitted. Starting materials.-4 - Acetamido - 8 - [4- N - (di - methylaminomethylene)sulphamoylphenylazo] - 5 - hydroxy - 1 - naphthalene sulphonyl chloride is prepared from sodium 4 - acetamido - 5 - hydroxy - 8 - (4 - sulphamoylphenylazo) - 1 - naphthalene sulphonate, DMF and thionyl chloride, the sulphonate being in turn prepared by coupling diazotized sulphanilamide with 8-acetamido-1-acetoxy-5- naphthalene sulphonic acid pyridine salt, with concomitant hydrolysis of acetoxy to hydroxy. Other intermediates of similar structure are prepared by analogous methods, e.g. 4-benzamido - 8 - [4 - (N - benzenesulphonylsulphamoyl)phenylazo] - 5 - hydroxy - 1 - naphthalene - sulphonic acid chloride is prepared from the sodium salt of the free acid and PCl 5 . 4 - Acetamido - 8 - (4 - chlorosulphonylphenylazo) - 5 - hydroxy - 1 - naphthalenesulphonyl chloride is prepared from sodium 4-acetamido-5- hydroxy - 8 - (4 - sulphamoylphenylazo) - 1- naphthalene sulphonate and chlorosulphonic acid and other intermediates of similar structure are prepared similarly. N-[5-hydroxy-8-(mfluorosulphonylphenylazo) - 1 - naphthyl] methanesulphonamide is prepared by diazotization and coupling. The corresponding m-chlorosulphonyl compound is prepared similarly, and is reacted with ethyl chloroformate to give N- [5 - ethoxycarbonyloxy - 8 - (m - chlorosulphonylphenylazo) - 1 - naphthyl]methanesulphonamide. Specification 1,405,662 is referred to, and compound XLIV thereof is disclaimed.