Toluene → HCID 9901114, compound

Participants

Reaction Steps

2-Amino-5-methylbenzoic acid (1.51 g, 10 mmol) was dissolved in pyridine (10 ml), and to this was added the crude octyl chlorothiolformate (28 mmol, assuming 100% from the first step) as a solution in toluene. After 2 h, the reaction was diluted with ethyl acetate and washed three times with 1M aqueous HCl, then saturated aqueous sodium bicarbonate, water and brine. The organic phase was dried (MgSO4) and concentrated in vacuo. Crystallisation from hexane gave the title compound (155 mg, 5%): δH (400 MHz, CDCl3) 0.91 (3H, t, J 7.0, Me), 1.30-1.34 (8H, m, 4×CH2), 1.44-1.50 (2H, m, SCH2CH2CH2), 1.79 (2H, qn, J 7.4, SCH2CH2), 2.46 (3H, s, ArMe), 3.16 (2H, t, J 7.3, SCH2), 7.38 (1H, d, J 8.2, ArH), 7.58 (1H, dd, J 8.2, 1.8, ArH), 7.93 (1H, s, ArH); m/z (ES+) 306 (MH+).

Provenance & Evidence