GB969286A - Process for the production of basic thymyl ethers - Google Patents

Abstract

The invention comprises compounds of general formula: <FORM:0969286/C1/1> where R represents a hydroxy, alkoxy, acyloxy, amino or acylamino group or a halogen atom and Hal represents chlorine, bromine or iodine; and acid addition salts thereof; and their preparation by (1) condensing a corresponding 4-R-thymyl b -haloethyl ether with ethylaminoethanol and thereafter halogenating the intermediate (4-R-thymyl) (N-ethyl-N-b -hydroxyethylamino-ethyl) ether with thionyl chloride or bromide, (2) forming the b -bromoethyl compounds from the b -chloroethyl compound by reaction with sodium bromide in ethanol, (3) forming the b -iodoethyl compounds from the b -chloroethyl compound by reaction with sodium iodide in ethanol or acetone, and (4) as described with reference to the examples wherein also (A) (4-acetamido-thymyl) (b -chloroethyl) ether is reacted with ethylamino-ethanol and product hydrolysed to yield (4-amino-thymyl) (N-ethyl-N-b -hydroxyethyl-amino-ethyl) ether dihydrochloride which is reacted with thionyl chloride to yield the corresponding b -chloroethyl compound which by diazotisation and acetylation yields (4-acetoxy-thymyl) (N-ethyl-N-b -chloroethyl-amino-ethyl) ether monohydrochloride, and (B) b -bromoethyl products are obtained from b -chloroethyl compounds by reaction with alkali metal bromides in alcohol or acetone. Compounds I are also said to be obtained by reacting 4-substituted-thymols with bis-(b -chloroethyl)-ethyl amine and sodium ethoxide which yields mainly (bis-(thymoxyethyl)-ethyl amines.