Water → N-[2-chloro-5-(3-morpholinobenzamido)phenyl]-3,4-dimethoxybenzamide

HRID 991421Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](Cl)=[O:11])[CH2:3][CH2:2]1.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([Cl:36])=[C:21]([NH:23][C:24](=[O:35])[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=2)[CH:22]=1.O>N1C=CC=CC=1>[Cl:36][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][CH:15]=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:8]=2)=[CH:22][C:21]=1[NH:23][C:24](=[O:35])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1

Participants

Conditions

Temperature: 115 °C

Procedure

3-Morpholinobenzoyl chloride (0.15 g) was added to a stirred solution of N-(5-amino-2-chlorophenyl)-3,4-dimethoxybenzamide (0.17 g) in pyridine (3 ml). The reaction mixture was stirred and heated to 115° C. for 18 hours. The mixture was allowed to cool and poured into water. The mixture was extracted with methylene chloride. The organic extract was dried (MgSO4) and evaporated. The resultant solid was azeotroped with toluene and triturated under diethyl ether to give the title compound (0.1 g), m.p. 147.9-148.3° C.;

Workup

temperatureto cool
extractionThe mixture was extracted with methylene chloride
extractionThe organic extract
dry with materialwas dried (MgSO4)
customevaporated
customThe resultant solid was azeotroped with toluene
customtriturated under diethyl ether

Sources & evidence

ORD record: ord-b44995c9e70244ae9b866686a38d709f
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465455B1

Reaction notes

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