Triethylamine → HCID 24772096, compound

Participants

Reaction Steps

Thiourea 4 (6 g, 18.3 mmol, 1 equiv.) was stirred in CH2Cl2 (110 mL) under N2 atmosphere. 5-Bromovaleryl chloride (3.65 g, 18.3 mmol, 1 equiv.) was added, followed by triethylamine (2.51 mL, 18.3 mmol, 1 equiv.). The beige suspension was stirred at rt for 4 h and diluted with CH2Cl2 (50 mL). The organic solution was washed with 1 M aqueous hydrochloric acid (1×50 mL), 10% aqueous sodium hydroxide (1×50 mL), and saturated brine (1×50 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The resulting brown foam was purified by flash chromatography on silica (50% ethyl acetate/petroleum ether) to give 5-bromo-pentanoic acid {4-[3-(4-tert-butyl-benzoyl)-thioureido]-phenyl}-amide (intermediate JH140) (6.76 g, 77%) as a yellow powder.

Provenance & Evidence