Methyl iodide → S,N-dimethyl-N'-nitroisothiourea

Participants

Reaction Steps

To a solution of 2-methyl-1-nitro-2-thiopseudourea (430 mg, 3.19 mmol) in DMF (3 ml) was added Cs2CO3 (1.10 g, 3.38 mmol) and MeI (0.30 ml, 4.82 mmol) and the reaction stirred overnight. The mixture was then diluted with water (10 ml) and EtOAc (40 ml) and the organic layer washed with brine (3×15 ml), dried (Na2SO4) and concentrated. The resultant yellow oil was purified by column chromatography on silica gel (EtOAc/Hexanes, 1:1) to afford S-methyl N-nitro-N′-methylcarbamimidothioate (56 mg, 11%) as a white solid. 1H NMR (CDCl3) δ 2.52 (s, 3H), 3.12 (d, 3H, J=6 Hz), 10.05 (br s, 1H).

Provenance & Evidence