Aziridine → HCID 9905397, compound

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Reaction Steps

A solution of N-(2,3-dihydroxypropyl)-5-chloro-2,4-dinitrobenzamide (Friedlos et al., J. Med. Chem., 1997, 40, 1270-1275) (0.50 g, 1.56 mmol) and aziridine (1.00 g, 0.023 mol) in EtOAc (100 mL) was stirred at room temperature for 18 h. After washing with water the solution was worked up to give 2 (0.43 g, 84%): mp (EtOAc/petroleum ether) 145-147° C., 1H NMR [(CD3)2SO] δ8.74 (t, J=5.7 Hz, 1H, NH), 8.64 (s, 1H, H-3), 7.43 (s, 1H, H-6), 4.85 (d, J=4 9 Hz, 1H, OH), 4.58 (t, J=5 7 Hz, 1H, OH), 3 62 (m, 1H, CHOH), 3.44-3.36 (m, 2H, CH2OH), 3.39-3.36 (m, 1H, CONHCHH), 3.16-3.09 (m, 1H, CONHC), 2 48 (s, 4H, aziridine-H); 13C NMR δ164.19 (s), 152.98 (s), 139.70 (s), 138.89 (s), 137 53 (s), 124 57 (d), 122.58 (d), 70.02 (d), 63.70 (t), 42.73 (t), 29.91 (t). Anal. Calcd. for C12H14N4O7. C, 44.18;H, 4.33; N, 17.17%. Found: C, 44.22; H, 4.25; N, 17 40%.

Provenance & Evidence