Ethylene Glycol → 2-Amino-5-methoxybenzene-1-thiol

Participants

Reaction Steps

A mixture of 2-amino-6-methoxybenzothiazole (15 g, 83.2 mmol), ethylene glycol (20.23 g, 0.33 mol) and 50% w/v KOH (100 ml) was heated under reflux for 24 h. On cooling to room temperature, toluene (60 ml) was added and the reaction mixture was cooled in an ice-bath and acidified with acetic acid (final pH 5-6). The reaction mixture was extracted with toluene (5×300 ml) and the combined organic extracts were washed with brine (2×200 ml), dried (MgSO4) and the solvent removed under reduced pressure to give the title compound (11.1 g, 86%) as a yellow solid which was used without further purification.

Provenance & Evidence