Benzyl Bromide → 4-Benzyl-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one
Reaction equation
[H-].[Na+].[F:3][C:4]([F:18])([F:17])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:12][O:13][C:14](=[O:16])[N:15]=2)[CH:6]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:19]([N:15]1[C:14](=[O:16])[O:13][N:12]=[C:11]1[C:7]1[CH:6]=[C:5]([C:4]([F:3])([F:17])[F:18])[CH:10]=[CH:9][N:8]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
Procedure
Into 2 ml of N,N-dimethylformamide was suspended 0.04 g of sodium hydride (60% oily), and 0.2 g of 3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one was added at room temperature. After stirring for 10 minutes, 0.22 g of benzyl bromide was added, and the mixture was stirred for 3 hours. Thereafter, the reaction solution was poured into an aqueous saturated ammonium chloride solution, followed by extraction with tert-butyl=methyl=ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.08 g of 4-benzyl-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (5)).
Workup
- additionwas added at room temperature
- stirringthe mixture was stirred for 3 hours
- extractionfollowed by extraction with tert-butyl=methyl=ether three times
- washwashed with an aqueous saturated sodium chloride solution
- dry with materialdried with anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e11c160c5511469d89cfa62d9e0248f2
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318776B2
Reaction notes
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