Benzyl Chloride → HCID 58957437, compound

Participants

Reaction Steps

To a solution of 3-allyl-5-benzoyl-2-thiohydantoin (0.098 g, 0.0003 mol) and benzyl chloride (0.042 g, 0.00033 mol) in tetrahydrofuran (2 mL) was added a solution of 1M potassium tert-butoxide in tetrahydrofuran (0.33 mL, 0.00033 mol) under argon. A cherry solid was formed in the reaction mixture. The resulting mixture was heated at reflux for 1 hr and then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (40 mL), washed with 3M HCl (2×20 mL) and brine (1×20 mL), filtered through 1 PS filter paper and concentrated under reduced pressure to give 0.13 g of a brown oil which solidified on standing. This solid was triturated with hexane (5 mL) once and then was dried under high vacuum. NMR (CDCl3) δ (10.9 s br, 1H), 8.6-8.9 (m, 2H), 7.3-7.9 (m, 8H), 4.7 (S, 2H), 4.4 (d, 2H).

Provenance & Evidence