Ammonia → HCID 21837948, compound

Participants

Reaction Steps

24.2 g (92.6 mmol) 5-(4-chlorophenyl)-pentyl bromide 60 in 60 ml ethanol was added to a solution of 10.6 g (0.139 mmol) thiourea in 40 ml ethanol. It was heated for 5 h to reflux, allowed to cool, admixed with 50 ml concentrated ammonia solution and again heated for 3 h to reflux. After cooling it was acidified to pH 1 with ca. 30 ml concentrated HCl and extracted twice with 150 ml ether. It was washed with saturated NaCl solution, dried over sodium sulfate and the solvent was removed on a rotary evaporator, 19.0 g (95%) 79 was obtained. A mixture of 5.00 g (16.3 mmol) 79, 2.25 g (16.3 mmol) potassium carbonate, 3.50 g (16.3 mmol) 6 and 50 ml dimethylformamide was stirred for 12 h at room temperature. It was admixed with water and extracted with ether. The ether phase was washed with water, dried over sodium sulfate and concentrated by evaporation. 7.1 g yellow oil which yielded 5.06 g (71%) of the ethyl ester of 27 after flash chromatography (toluene/heptane 1:2).

Provenance & Evidence