Ammonia → 4-[3-[2-(4-Chlorophenylsulphonylamino)-ethyl]-phenoxy]-butyramide

Participants

Reaction Conditions

Reaction Steps

To a solution cooled to -10° C. of 100 ml abs. THF, 4.32 g (43 mmol)triethylamine and 14.4 g (36 mmol) 4-[3-[2-(4-chlorophenylsulphonylamino)-ethyl]-phenoxy]butyric acid one slowly adds dropwise a mixture of 4.02 g (37 mmol) chloroformic acid ethylester and 30 ml abs. THF. One allows to come to room temperature, stirs a further 30 min and filters off with suction the precipitated triethylaminehydrochloride. The filtrate is then gassed with ammonia with ice cooling. It is then stirred for 6 hrs. at room temperature, evaporated and mixed with 2N HCl. One adds ethyl acetate thereto, mixes up very vigorously and separates the phases. The ethyl acetate phase is shaken out twice with bicarbonate solution and twice with water, then dried with Na2SO4 and evaporated. After recrystallisation from ethyl acetate, one obtains colourless crystals. Yield: 12.8 g (89% of theory); m.p. 110°-112° C.

Provenance & Evidence