Phosgene → HCID 9815014, compound

Participants

Reaction Steps

1-Octanethiol (0.71 ml, 4.1 mmol) was dissolved in THF (10 ml). To this solution was added a solution of phosgene (20% in PhMe, 3.5 ml, 7.4 mmol). After 2.5 h the reaction vessel was purged with nitrogen to remove excess phosgene and hydrogen chloride, the vented gas being passed through a scrubber containing dilute aqueous sodium hydroxide. The crude octyl chlorothiolformate solution was used directly. 2-Amino-4-methylbenzoic acid (151 mg, 1 mmol) was dissolved in pyridine (0.5 ml) and DCM (5 ml). To this was added one quarter of the crude octyl chlorothiolformate solution (1 mmol, assuming 100% from the first step). After 24 h, the reaction was diluted with ether and washed with 1M aqueous HCl and brine. The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexane gradient) to give a solid which was triturated with acetonitrile to afford the title compound (43 mg, 14%): δH (400 MHz, CDCl3) 0.82 (3H, t, J 6.7, Me), 1.21-1.24 (8H, m, 4×CH2), 1.37-1.41 (2H, m, SCH2CH2CH2), 1.68-1.72 (2H, m, SCH2CH2), 2.40 (3H, s, ArMe), 3.08 (2H, t, J 7.4, SCH2), 7.16 (1H, d, J 8.0, ArH), 7.19 (1H, d, J 1.4, ArH), 7.93 (1H, d, J 8.0, ArH); m/z (ES+) 306 (MH+).

Provenance & Evidence