Chloroacetonitrile → HCID 54556287, compound

Participants

Reaction Steps

A solution of 5-[4-(2-phenylethoxy)phenylmethylene]-2,4-thiazolidinedione Example 4 (1.0 g, 3.07 mmol) in 25 ml dry DMF was treated with NaH (0.1 g, 4.2 mmol) and stirred at room temperature for 10 min. The mixture was treated with chloroacetonitrile (0.3 g, 4 mmol) and stirred at room temperature for 24 h. The mixture was poured into 500 ml ice water, and the resulting tan solid was collected by filtration, washed with water, and dried to give the desired product in 75% (1.0 g) yield; mp 155-157° C.; NMR(CDCl3TMS): δ3.13 (t, 2H, ArCH2), 4.25 (t, 2H, OCH2), 4.60 (s, 2H, CH2CN), [7.00 (d, 2H), 7.45 (d, 2H) OPh], 7.26 (m, 5H, Ph), 7.94 (s, 1H, C=CH); Anal calcd for C20H16N2O2S, MW 364.42: C, 65.92; H, 4.43; N, 7.69; S, 8.80. Found: C, 66.15; H, 4.24; N, 7.93; S, 8.69. Mass spec m/e 365(M+1).

Provenance & Evidence