Methyl iodide → HCID 58980898, compound

Participants

Reaction Steps

Methyl 4-chlorobenzenecarbodithioate (0.690, 3.4158 mmol) and cyanamide (0.1436 g, 3.1458 mmol) were taken up in dry methanol (10 mL). Potassium methoxide (0.2396 g, 3.4158 mmol) was added. The reaction was stirred at RT for 3 h. The reaction mixture was concentrated to dryness to give a red solid. The residue was taken up in DMF (10 mL) and methyl iodide (0.727 g, 5.123 mmol) were added. The reaction was stirred for 2 hours, then diluted with EtOAc (50 mL). The organics were washed with water (3×100 mL), dried over MgSO4, filtered and concentrated. The residue was taken up in dry methanol (10 mL) and thioglycolate methyl ester (0.739 g, 9.96 mmol) was added, followed by triethylamine (1.3 mL). The reaction was stirred overnight at RT. The precipitate was collected to give 0.16 g (0.5970 mmol, 17%) of product. 1H NMR (CDCl3) δ 7.85 (d, 2H, J=8.4 Hz), 7.40 (d, 2H, J=8.6 Hz), 5.89 (bs, 2H), 3.85 (s, 3H).

Provenance & Evidence