3-(Chloromethyl)benzoyl chloride → N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-chloromethylbenzamide

HRID 967907Notes

Reaction equation

HRID 967907 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[NH2:12][C:13]1[CH:14]=[C:15]([NH:20][C:21](=[O:34])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:23]=2)[CH:16]=[CH:17][C:18]=1[CH3:19]>>[CH3:19][C:18]1[CH:17]=[CH:16][C:15]([NH:20][C:21](=[O:34])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[CH:23]=2)=[CH:14][C:13]=1[NH:12][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([CH2:2][Cl:1])[CH:4]=1

Participants

3

Reactant 2

HCID 27333243-(Chloromethyl)benzoyl chlorideHCID 11301391N-(3-amino-4-methylphenyl)-3-morpholinobenzamide

Product 1

HCID 22291061N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-chloromethylbenzamideYield 98%

Procedure

Using an analogous procedure to that described in Example 63, 3-chloromethylbenzoyl chloride was reacted with N-(3-amino-4-methylphenyl)-3-morpholinobenzamide. There was thus obtained the title compound in 98% yield; NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 3.17 (m, 4H), 3.75 (m, 4H), 4.85 (s, 2H), 7.13 (d, 1H), 7.22 (d, 1H), 7.34 (m, 2H), 7.44 (s, 1H), 7.54 (m, 2H), 7.65 (d, 1H), 7.79 (s, 1H), 7.95 (d, 1H). 8.03 (s, 1H), 9.96 (s, 1H), 10.12 (s, 1H); Mass Spectrum: M+H+ 464.

Sources & evidence

ORD record
ord-5b5db5023b5247f29e9b6365350ac1fa
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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