GB262141A - Manufacture of thiazole derivatives of 1:4-naphthoquinone - Google Patents

Abstract

262,141. I. G. Farbenindustrie Akt.- Ges., (Assignees of Akt.-Ges. f³r Anilin- Fabrikation). Nov. 28, 1925, [Convention date]. Thiazoles.-Thiazole derivatives of 1: 4-naphthoquinone are obtained by condensing 2 amino- 3-mercapto-1 : 4-napthoquinone with an aldehyde. The intermediate products first obtained pass into thiazoles by the action of atmospheric oxy- and may be used directly for vat dyeing. In an example, 2-amino-3-mercapto-1: 4.naphthoquinone is condensed with benzaldehyde; greenish-yellow crystals are obtained which form a blue-red vat, dyeing cotton a greenish yellow. fast to chlorine and soap, when dissolved in caustic soda and hydrosulphite. The finished dyestuff may be obtained by introducing air into the solution. The properties of the thiazole derivatives obtained from the following aldehydes are tabulated :-Glyoxal, 1-naphthaldehyde, artetrahydronaphthalene-1-aldehyde, 4-aminobenzaldehyde, 4-dimetbylaminobenzaldehyde, 2.chlor- 4-dimethylaminobenzaldehyde, and terephthalic aldehyde. Some of the products dye animal fibres as well as vegetable fibres in the vat. and compounds containing sulpho groups, e.g. the product obtained by condensing 2-amino-3-mercapto-1: 4-naphthoquinone with benzaldehyde sulphonic acid, dye wool without being previously vatted. 2-Amino-3-mercapto-1 : 4-naphthoquinone is obtained by treating 2-amino-3-chlor-1 : 4-naphthoquinone with sodium sulphide. ar-Tetrahydronaphthalene-1-aldehyde is made from tetrahydronaphthalene by converting it into its 1-#-aminomethyl derivative (by condensing with #-chlormethylphthalimide and treating the product in succession with an alkali and an acid, according to the process described in Specification 249,883), condensing with 4-nitra-1-chlorbenzene-2-sulphonic acid, and oxidizing the product by means of bichromate and sulphuric acid.