Methyl isothiocyanate → HCID 19876107, compound

Participants

Reaction Steps

A vigorously stirred solution of 2-(6-chloropyrid-3-yl)cyclohexanone (0.36 g 1.7 mmol) in anhydrous tetrahydrofuran (10 ml) under argon at -15° C. was treated with potassium t-butoxide (0.19 g, 1.7 mmol). The resulting mixture was stirred for 2 hours at room temperature before the addition of a solution of methyl isothiocyanate (0.12 g, 1.7 mmol) in dry tetrahydrofuran (2 ml). The mixture was stirred for a further 48 hours at room temperature, concentrated in vacuo and the residue treated with water (30 ml) and extracted with ethyl acetate (50 ml). The organic extract was dried over magnesium sulphate and then concentrated in vacuo (30° C.; 14 mmHg) to give a yellow oil which was purified by flash chromatography over silica gel eluting with ethyl acetate: hexane 4:6 to give (±)-N-methyl-2-oxo-1-(6-chloropyrid-3-yl) -cyclohexanecarbothioamide (0.25 g) m.p. 172°-3° C. NMR (CDCl3) 1.64-2.14(m 4H); 2.4-2.65(m 2H); 2.7-2.8(m 2H); 3.14-3.16(d,3H); 7.26-7.34 (ddd,1H); 7.6-7.66(dd,1H); 8.2(d,1H); 8.84-9.06 (broad singlet, 1H). Calculated for C13H15ClN2OS; C,55.2%; H,5.35%; N,9.91%, C1,12.5%; Found C,55.3%; H,5.3%; N,9.8%;C1,12.6%.

Provenance & Evidence