Dichloromethane → HCID 10577722, compound

Participants

Reaction Steps

Triphenylmethyl chloride (2.67 g, 9.58 mmol) was added to a stirred, room temperature solution of 5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione [(V), from Example 12, 1.30 g, 4.79 mmol], triethylamine (0.67 mL, 4.79 mmol) and dichloromethane (6.5 mL). After 1 h, water (300 mL) was added and the organic material was extracted with ethyl acetate (2×200 mL). The combined extracts were dried (brine, MgSO4), concentrated and purified by flash chromatography (4:1 petroleum ether:ethyl acetate) to provide the title compound as a white solid (1.1 g, 45%): mp 105°-110° C.; NMR (CDCl3): δ7.85 (d, J=8.3 Hz, 2H, ArH), 7.48 (d, J=8.1 Hz, 6H, CPh3H), 7.38 (d, J=8.3 Hz, 2H, ArH),7.23 (m, 9H, CPh3H), 5.13 (s, 1H, CH), 2.46 (s, 3H, CH3).

Provenance & Evidence