Benzoyl chloride, 3,4-dichloro- → N-(4-Chlorophenyl)-N'-{[4-(3,4-dichlorobenzoyl)morpholin-2-yl]methyl}urea

HRID 1371439Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[O:10])=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[Cl:29])[C:23](Cl)=[O:24]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15]([C:23](=[O:24])[C:22]3[CH:26]=[CH:27][C:28]([Cl:29])=[C:20]([Cl:19])[CH:21]=3)[CH2:14]2)=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 22 °C

Procedure

To a stirred solution of Intermediate 9 (0.05 g) was added a solution of 3,4-dichlorobenzoyl chloride (42.7 mg) in N,N-dimethylformamide (7 ml). The mixture was stirred at 22° C. for 15 h before the solvent was evaporated in vacuo. The residue was purified by eluting through a 1 g silica solid phase extraction cartridge (Varian Bondelut), eluting sequentially with dichloromethane, ether, ethyl acetate, acetone, acetonitrile and methanol, to give the title compound as a white solid (0.080 g). LC/MS (System A) Rt 3.10 min, Mass Spectrum m/z 442 [MH+].

Workup

customwas evaporated in vacuo
customThe residue was purified
washby eluting through a 1 g silica solid phase extraction cartridge (Varian Bondelut)
washeluting sequentially with dichloromethane, ether, ethyl acetate, acetone, acetonitrile and methanol

Sources & evidence

ORD record: ord-7bc4bd1fb37f48949c6fd432231ab5a8
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157457B2

Reaction notes

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