Triethylamine → 1H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-, carbamate (ester)

Participants

Reaction Conditions

Reaction Steps

In 7 ml of dry tetrahydrofuran was dissolved 700 mg (1.6 mmol) of the alcohol (137c), and after the solution was cooled to -40° C., 450 mg (2.4 mmol) of trichloroacetyl isocyanate was added and the temperature was elevated gradually to room temperature. After stirring for 30 minutes, 2 ml of water and 1 ml of triethylamine were added and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol-ethyl acetate) and recrystallized from ethyl acetate-n-hexane to provide 610 mg (yield 79%) of Compound I-150 as crystals. mp 114-115° C.

Provenance & Evidence