4-(Chloromethyl)benzoyl chloride → N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]4-chloromethylbenzamide
Reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:14]=[C:15]([NH:20][C:21](=[O:31])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]([CH3:30])[CH3:29])[CH:23]=2)[CH:16]=[CH:17][C:18]=1[CH3:19]>>[CH3:30][N:28]([CH3:29])[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:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([CH2:2][Cl:1])=[CH:4][CH:5]=2)[CH:14]=1)=[O:31]Participants
3
Procedure
4-Chloromethylbenzoyl chloride was reacted with N-(3-amino-4-methylphenyl)-3-dimethylaminobenzamide using an analogous procedure to that described in Example 37 except that the reaction product was triturated under water rather than under 2N aqueous hydrochloric acid solution. There was thus obtained the title compound; NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 2.95 (s, 6H), 4.28 (s, 2H), 6.9 (d, 1H), 7.21 (m, 3H), 7.29 (d, 1H), 7.58 (d, 3H), 7.8 (s, 1H), 7.96 (d, 2H), 9.9 (s, 1H), 10.08 (s, 1H); Mass Spectrum: M−H− 420.
Workup
- customwas triturated under water rather than under 2N aqueous hydrochloric acid solution
Sources & evidence
- ORD record
- ord-9760db3b90f34f1d898c8177ec1a2202
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06956037B2
Reaction notes
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