3-(Chloromethyl)benzoyl chloride → N-[5-(3-trifluoromethylbenzamido)-2-methylphenyl]-3-(chloromethyl)benzamide

HRID 1369528Notes

Reaction equation

HRID 1369528 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:32])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH:16]=[CH:17][C:18]=1[CH3:19]>>[F:29][C:28]([F:30])([F:31])[C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([NH:20][C:15]1[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([NH:12][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([CH2:2][Cl:1])[CH:4]=2)[CH:14]=1)=[O:32]

Participants

3

Reactant 2

HCID 27333243-(Chloromethyl)benzoyl chlorideHCID 11529455N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 22291017N-[5-(3-trifluoromethylbenzamido)-2-methylphenyl]-3-(chloromethyl)benzamideYield 94%

Procedure

Using an analogous procedure to that described in Example 37, 3-chloromethylbenzoyl chloride was reacted with N-(3-amino-4-methylphenyl)-3-trifluoromethylbenzamide to give the title compound in 94% yield; NMR Spectrum: (DMSOd6) 2.2 (s, 3H), 4.85 (s, 2H), 7.25 (d, 1H), 7.6 (m, 3H), 7.8 (m, 2H), 7.95 (d, 2H), 8.05 (s, 1H), 8.16 (m, 2H), 9.96 (s, 1), 10.44 (s, 1H); Mass Spectrum: M−H− 445.

Sources & evidence

ORD record
ord-2e382149eb4d462da1578dea70bd3153
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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