Oxalyl chloride → 3-bromo-N-cyclopropyl-4-methylbenzamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH:18]1([NH2:21])[CH2:20][CH2:19]1>C1C=CC=CC=1.ClCCl.CN(C)C=O.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:21][CH:18]1[CH2:20][CH2:19]1)=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Procedure
A stirred, cooled (ice bath) solution of 3-bromo-4-methyl-benzoic acid (Aldrich, 5 g, 23.25 mmol) in benzene (50 mL), dichloromethane (10 mL) and N,N-dimethylformamide (0.5 mL) was treated with oxalyl chloride (4 mL, 46.5 mmol). The reaction mixture was allowed to warm to ambient temperature over 3 h. The volatiles were then distilled off in vacuo, the residue was diluted with anhydrous dichloromethane (50 mL) under argon, cooled (ice bath) and treated with 4-(dimethylamino)pyridine (5.67 g, 46.5 mmol) followed by cyclopropyl amine (1.93 mL, 27.9 mmol). After 3 h, the reaction mixture was diluted with dichloromethane and washed with water. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title product that was used as such for the next step (6.0 g, ˜100%).
Workup
- distillationThe volatiles were then distilled off in vacuo
- additionthe residue was diluted with anhydrous dichloromethane (50 mL) under argon
- temperaturecooled (ice bath)
- washwashed with water
- dry with materialThe organic phase was dried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-43650ba22a6449409b0d8cb8c0237e1e
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638648B2
Reaction notes
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