Process for the preparation of styryl dyestuffs

Claim 1

Process for the preparation of a styryl dyestuff free of ionogenic groups of the formula ##STR32## wherein R' 1 is a straight-chain, branched, cyclic, saturated or unsaturated C 1 -C 6 -alkyl radical which is unsubstituted or which is substituted with a member selected from the group consisting of phenyl, substituted phenyl, C 1 -C 5 -alkoxy; C 1 -C 5 -alkylmercapto, phenyloxy, substituted phenyloxy, phenylmercapto, substituted phenylmercapto, heterylmercapto, (C 1 -C 5 -alkyl)-carbonyl-oxy, phenylcarbonyloxy, substituted phenylcarboxyloxy, (C 1 -C 5 )-alkoxy-carbonyloxy, (C 1 -C 5 -alkylamino)-carbonyloxy, phenylaminocarbonyloxy, substituted phenylaminocarbonyloxy, (C 1 -C 5 -alkoxy)-carbonyl, C 1 -C 5 -alkyl sulphonyl, phenyl sulphonyl, substituted phenylsulphonyl, halogen, --CN, or ##STR33## in which Q is CO, SO 2 or CH 2 ; A is ortho-arylene or C 2 -C 3 -alkylene; or R' 1 is ##STR34## in which Z is a direct bond, O, s, so, so 2 , nr, --o--co--o--, ##STR35## --O--arylene--O--, --CO--O--alkylene--O--CO-- or --OCONH-arylene-NHCOO--; phenyl or substituted phenyl; R' 2 is hydrogen or R' 1 ; R' 3 -r' 6 are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, bromine or chlorine; or R' 1 together with R' 3 or R' 5 conjointly form the remaining members of a non-aromatic 5-membered or 6-membered ring system which optionally contains oxygen or sulphur; said heteryl is selected from the group consisting of furane, thiophene, pyridine, pyrimidine, benzoxazole, benzthiazole, benzimidazole and the foregoing heterocyclic radicals substituted with C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, halogen, nitrile, C 2 -C 5 -carbalkoxy or phenyl, said alkylene radicals are C 1 -C 6 -alkylene; and said arylene radicals are phenylene or phenylene substituted by C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, C 2 -C 5 -alkoxycarbonyl, halogen, nitro, --CN or phenoxy; said substituted phenyl is substituted with C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, C 2 -C 5 -alkoxycarbonyl, halogen, nitro, nitrile or phenoxy; X' is CN, (C 1 -C 4 -alkyl)-carbonyl, substituted (C 1 -C 4 -alkyl)-carbonyl, (C 1 -C 4 -alkoxy)-carbonyl, substituted (C 1 -C 4 -alkoxy)-carbonyl, heterylcarbonyl, phenoxycarbonyl, substituted phenoxycarbonyl, C 1 -C 4 -alkyl-sulphonyl, substituted C 1 -C 4 -alkylsulphonyl, carbamoyl, phenyl-(C 1 -C 4 -alkoxy)-carbonyl, N-(C 1 -C 4 -alkyl)-carbamoyl, substituted N-(C 1 -C 4 -alkyl)-carbamoyl, N,N-di(C 1 -C 4 -alkyl)-carbamoyl, or substituted N,N-di(C 1 -C 4 -alkyl)-carbamoyl; wherein in X' said substituted alkyl and alkoxy radicals are substituted by OH, F, Cl, Br, CN, C 1 -C 3 -alkoxy or C 2 -C 4 -alkylcarbonyloxy, and said substituted phenyl or phenoxy radicals are substituted by Cl, F, Br, C 1 -C 4 -alkoxy, NO 2 , CN, C 1 -C 4 -alkyl, or phenoxy, and "heteryl" is defined as above; comprising a one-pot reaction in which an amine of the formula ##STR36## is treated with at least 1 equivalent of a Vilsmeier reagent; unconverted Vilsmeier reagent is decomposed by the addition of aliphatic alcohol; the pH value is adjusted to above 4 by addition of base; and the reaction product without any intermediate isolation is reacted with a methylene-active compound of the formula ##STR37##