1,3-Dioxolane-2-ethylamine → 4,5-Dibromo-N-[2-(1,3-dioxolan-2-yl)ethyl]pyrrole-2-carboxamide

Participants

Reaction Steps

A solution of 2-(2-aminoethyl)-1,3-dioxolane (2.4 g, 20.6 mmol) and 4,5-dibromopyrrol-2-yl trichloromethyl ketone (7.6 g, 20.5 mmol) in 30 mL of acetonitrile was stirred at room temperature for 16 h. The reaction mixture was filtered and the precipitate 11 (6.8 g, 90%) was collected as a colorless solid: mp 155-157° C.; 1H NMR (CDCl3) d 1.99 (dt, 2H, J=6.0, 4.2), 3.61 (dt, 2H, J=6.0, 5.6), 3.92 (m, 2H), 4.05 (m, 2H), 5.00 (t, 1H, J=4.2), 6.51 (d, 1H, J=2.8), 6.66 (bs, 1H), 10.57 (bs, 1H); 13C NMR (CD3COCD3) d 34.3 (e), 35.5 (e), 65.4×2 (e), 99.4 (e), 103.4 (o), 105.4 (e), 113.0 (o), 129.1 (e), 160.0 (e); IR (nujol) 3358, 1646, 1569, 1412, 1372 cm−1; UV (CH3OH) 1max 275, 233, 214 (sh) nm; MS m/z (relative intensity) 371 (M++5, 50), 369 (M++3, 100), 367 (M++1, 50), 289 (13), 118 (25), 101 (50), 73 (30); Anal. Calcd for C8H10N2O2Br2: C, 32.63; H, 3.29; N, 7.61; Found: C, 32.77; H, 3.17; N, 7.51.

Provenance & Evidence