Methyl isothiocyanate → HCID 19780562, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (±)-2-phenylcyclohexanone (3.0 g, 17.2 mmol) at -15° C. in tetrahydrofuran (40 ml) was treated with potassium t.-butoxide (1.9 g, 17.2 mmol) during 2 minutes. After 15 minutes at -15° C., a solution of methyl isothiocyanate (1.38 g, 19 mmol) in tetrahydrofuran (20 ml) was added dropwise during 2 minutes and the resulting solution was stirred for 3 hours at 0° C. Water (200 ml) followed by chloroform (200 ml) were added to the reaction mixture and the aqueous layer was extracted with chloroform (200 ml). The combined organic extracts were washed with brine (150 ml) then dried over sodium sulphate. Concentration in vacuo (30° C.; 14 mm Hg) afforded a crude oil (4.2 g) which was purified by flash chromatography over silica gel eluting with a 1:1 mixture of diethyl ether and hexane to give (±)-N-methyl-2-oxo-1-phenylcyclohexanecarbothioamide (1.5 g, 6.1 mmol) m.p. 86° C. N.M.R. (CDCl3) 1.62-2.05 (c, 4H), 2.42-2.56 (m, 2H), 2.64-2.84 (ddd, 1H), 3.0-3.18 (c, 4H), 7.23-7.45 (c, 5H) 8.72-9.06 (broad singlet, 1H). Found C, 68.3; H, 7.2; N, 5.8; S, 13 0%, C14H17NOS requires C, 68.0; H, 6.9; N, 5.7; S, 13.0%.

Provenance & Evidence