Acetonitrile → Cyclooctylthiourea

Participants

Reaction Steps

To a stirred solution of cyclooctyl isothiocyanate (7.26 g, 42.9 mmol) in 70 ml of CH3CN was added 8.5 ml of 15N NH4OH (130 mmol). The reaction progress was monitored by thin layer chromatography (TLC); 1/1 EtOAc/hexane. After 3 days, the reaction solution was concentrated, dissolved in 50 ml of ethyl acetate and washed with water (25 ml) and brine (aqueous saturated NaCl) (3×25 ml ea.). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica gel, 3/7 EtOAc/hexane) to yield 6.25 g (78.2%) of the desired thiourea. PMR(CDCl3)ppm 6.5 (bs, 1H), 6.00 (s, 2H), 4.35 (bs, 1/2H), 3.45 (bs, 1/2H), 2.1-1.3 (m, 14H). The melting point (MP) was 93°-95° C.

Provenance & Evidence