4-Chlorobenzylamine → N-(4-Chlorobenzyl)-6-iodo-4-oxo-4H-1,2-benzoxazine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 6-iodo-4-oxo4H-1,2-benzoxazine-3-carboxylate (Preparation 17, 48 mg) and 4-chlorobenzylamine (41 mg) and toluene (1 mL) is heated to 100° C. for 2 minutes. The mixture is cooled and concentrated in vacuo, and the residue is crystallized from ethanol-ether mixture to give 0.60 g (48%) of the title compound. Physical characteristics: mp 188-190° C.; 1H NMR (400 MHz, DMSO-d6) δ 4.49, 7.41, 7.59, 8.25, 8.32, 9.2; IR (drift) 3284, 1680, 1656, 1599, 1571, 1490, 1453, 1433, 1199, 1158, 928, 921, 819, 782, 619 cm−1; MS (FAB) m/z 441 (MH+, 65); HRMS (FAB) m/z 440.9507 (C16H10ClIN2O3+H). Anal. Found: C, 43.56; H, 2.43; N, 6.32; Cl, 8.04.

Provenance & Evidence