1,4-Diisocyanatobenzene → HCID 23296770, compound

Participants

Reaction Steps

The same general procedure as reported in Example 13 was followed. 1,4-Phenylene diisocyanate (3.2 g, 20 mmol), N-(1-ethylpropyl)hydroxylamine (4.3 g, 42 mmol), and dichloromethane (200 ml) were combined. The product formed as a precipitate. Purification by recrystallization from N,N-dimethylformamide.backslash.water yielded 4.6 g of the desired product as a white powder: MP: 202.0° C. (decomp); 1H NMR (300 MHz, DMSO): δ 9.13 (s, 2H), 8.72 (s, 2H), 7.44 (s, 4H), 3.96-3.87 (septet, J=4.7 Hz, 2H), 1.60-1.33 (m, 8H), 0.84 (t, J=7.3 Hz, 12 H); 13C NMR (75 MHz, DMSO): δ 157.9, 134.0, 119.3, 59.6, 24.6, 11.1; IR (KBr): 3401, 3134, 2964, 2923, 2873, 1634, 1541, 1462, 1412, 1269, 1218, 1159, 1103, 1060, 833, 755, 736 cm-1 ; MS (FAB): m/e 367.2331 (367.2345 calc'd for C18H31N4O4, M+H); Anal. calc'd for C18H30N4O4 : C, 59.00; H, 8.25; N, 15.29. Found: C, 58.72; H, 8.34; N, 15.28.

Provenance & Evidence