Ammonia → {[(2R)-oxolan-2-yl]methyl}thiourea

Participants

Reaction Steps

To a 0° C. solution of (R)-(tetrahydrofuran-2-yl)methanamine (5.0 g, 49.5 mmol) and triethylamine (690 uL, 4.95 mmol) in tetrahydrofuran (100 mL) was added carbon disulfide (5.65 g, 74.3 mmol). Stirring was continued for 0.5 hour followed by the dropwise addition of 30% hydrogen peroxide (5.6 g, 49.5 mmol) so that the temperature was maintained below 40° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic extract was dried (Na2SO4), filtered and concentrated to afford an oil. The residue was dissolved in tetrahydrofuran, and treated with 7 N ammonia in methanol (14.3 mL, 100 mmol). The precipitate was collected by filtration and washed with water to afford the title compound.

Provenance & Evidence