Methylamine → 3-Mercapto-N-methylbenzamide

Participants

Reaction Steps

To a solution of 3-mercaptobenzoic acid (1.00 g, 6.49 mmol) in ethyleneglycol-dimethylether (10 ml) was added N-methylmorpholine (1.5 ml, 13.6 mmol) and iso-butylchloroformate (1.77 ml, 13.6 mmol) under a flow of nitrogen at 0° C. The clear solution quickly became a thick paste. After stirring for one hour the reaction was filtered and then treated with 2M methylamine in THF (7 ml, 14 mmol). The reaction was stirred for two days at room temperature and then treated with 0.5M sodium methoxide in methanol (14 ml). The reaction was stirred for three hours, then quenched with 2N HCl until pH=4 and concentrated in vacuo to a semi solid. This was dissolved in H2O (50 ml), basified (2N NaOH, pH=10), washed with CHCl3 (2×50 ml), acidified (2N HCl, pH=2) then extracted with CHCl3 (50 ml) and ethyl acetate (50 ml). The organic extracts were combined, dried (MgSO4) then concentrated in vacuo to a colourless oil (570 mg).

Provenance & Evidence