Sodium hydride → HCID 22004136, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-hydroxy-1-phenylbenzimidazole (Example 14) (0.88 g, 4.10 mmol) in 1:1 THF/DMF (15 mL) was added dropwise under nitrogen to a stirred suspension of NaH (0.24 g of a 50% dispersion in oil, 5.00 mmol) in THF (10 mL). After 10 minutes a solution of dimethylthiocarbamyl chloride (0.57 g, 4.6 mmol) in THF (5 mL) was added and the solution was warmed at 60° C. for 1 hour. The cooled solution was partitioned between ether and 2N KOH and the organic portion was worked up and chromatographed on silica. Elution with EtOAc/petroleum ether (7:3) gave the O-benzimidazolyl dimethylthiocarbamate (0.76 g, 65%), mp (EtOAc/petroleum ether) 173-174.5° C.

Provenance & Evidence