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

HRID 411201Notes

Reaction equation

[I:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][N:9]=[C:8]([C:11]([O:13]CC)=O)[C:7](=[O:16])[C:6]=2[CH:17]=1.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:11]([C:8]2[C:7](=[O:16])[C:6]3[CH:17]=[C:2]([I:1])[CH:3]=[CH:4][C:5]=3[O:10][N:9]=2)=[O:13])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

temperatureThe mixture is cooled
concentrationconcentrated in vacuo
customthe residue is crystallized from ethanol-ether mixture

Sources & evidence

ORD record: ord-a52eaa31ccdf46f4a051c0ad40da61e6
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559145B2

Reaction notes

Loading…