N-bromobutanimide → HCID 68494779, compound

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([Br:17])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

A mixture of N-benzyl-3-methylthiophene-2-carboxamide (6.63 g, 28.66 mmol) and N-bromosuccinimide (5.10 g, 28.66 mmol) in anhydrous acetonitrile (70 mL) was stirred at ambient temperature for 18 h, and diluted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (4×100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate/hexanes to afford the title compound as a colorless solid (6.48 g, 73%): 1H NMR (300 MHz, CDCl3) δ 7.40-7.29 (m, 5H), 6.87 (s, 1H), 5.95 (br s, 1H), 4.59 (d, J=5.7 Hz, 2H), 2.47 (s, 3H); MS (ES+) m/z 310.2 (M+1), 312.2 (M+1).