1,1'-Thiocarbonyldiimidazole → HCID 86590647, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−20° C.) solution of 1,1-thiocarbonyldiimidazole (811 mg, 4.415 mmol) (Aldrich) in N,N-dimethylformamide (11 mL) was added dropwise a solution of [3-(4-aminophenoxy)propyl]-ethyl-carbamic acid tert-butyl ester (1.175 g, 3.99 mmol) (from Step B above) in N,N-dimethyl-formamide (11 mL) over 25 minute. After the addition was complete, the mixture was stirred at −20° C. for 20 minutes and then at room temperature for 1 hour. Ice-water was added and the mixture was extracted with ether. The ether layer was dried (Na2SO4), filtered, and evaporated. The residue was purified on silica gel with 85:15 hexane/ethyl acetate to give ethyl-[3-(4-isothiocyanatophenoxy)propyl]carbamic acid tert-butyl ester (1.24 g, 92% yield). HRMS, Observed: 336.1496; Calcd for M+:336.1508.

Provenance & Evidence