GB861521A - Novel thioxanthene derivatives and salts thereof and a process for the manufacture ofsame - Google Patents

Abstract

The invention comprises 9-substituted thioxanthenol-(9)s in which the 9-substituent is a dialkylaminoalkyl group in which each of the alkyl groups of the dialkylamino moiety contain up to 4 carbon atoms and may be joined directly or through an oxygen, sulphur or nitrogen atom to form with the nitrogen atom of the amino group a 5- or 6-membered ring and in which the remaining alkyl group contains from 3 to 7 carbon atoms, and the corresponding compounds containing in one or more of positions 1 to 8 one or more alkyl or alkoxy groups or halogen atoms; and acid-addition salts thereof; and the preparation thereof by condensing the appropriate thioxanthone with an organo metallic derivative of the appropriate tertiary-amino-alkyl group and hydrolysing the metal containing condensation product so obtained. Organo-metallic compounds referred to are those of magnesium, lithium and zinc, and the use of Grignard reagents is preferred. The hydrolysis may be effected with aqueous ammonium chloride. Examples describe the preparation of 9-(gamma-dimethylamino-propyl)-thioxanthenol-(9) and the p corresponding 2-, 3- and 4-chloro-, 2-bromo-, 2-fluoro-, 2-methyl-, 1-, 2-, 3- and 4-methoxy-, 1-chloro-4-methoxy-1 - methyl - 4 - methoxy -, 1 - methyl - 4-chloro -, 1 - chloro - 4 - methyl -, 2 - chloro - 7-methoxy -, and 2:7 - dibromo - compounds. The preparation of the d-tartrate of 2-chloro-9-(gamma - dimethylamino - propyl) - thioxanthenol-(9) is also described. Thioxanthone and substituted thioxanthone starting materials are prepared by condensation of thiosalicylic acid or substituted thiosalicylic acids with benzene or appropriately substituted benzenes; or by condensation of diazo-anthranilic acid or appropriately substituted diazoanthranilic acids with thiophenol or appropriately substituted thiophenols and subsequent cyclization. The preparation of 2-chlorothioxanthone via 41-chloro-2-carboxy-diphenyl sulphide and the corresponding 3- and 4-chloro, 2-bromo and 2-fluoro compounds by a similar method; of 4-methoxy-thioxanthone via 6-methoxy - 21 - carboxy - diphenyl sulphide and the corresponding acid chloride; of 3-methoxy-thioxanthone via 5 - methoxy - 2 - carboxy - diphenyl sulphide and the corresponding acid chloride and of 1-methoxy-thioxanthone by a similar method; of 2 - chloro - 7 - methoxythioxanthone via 4- methoxy - 41 - chloro - 21-carboxy-diphenyl sulphide and the corresponding acid chloride; and of 2:7-dibromo-thioxanthone by bromination of thioxanthone is described. Specification 829,763 also is referred to.