Water → (3-chloro-5-trifluoromethyl-2-pyridyloxymethyl)-alpha-methoxy-N-methyl-phenylacetamide
Reaction equation
OC[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([O:14][CH3:15])[C:10]([NH:12][CH3:13])=[O:11].[H-].[Na+].Cl[C:19]1[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][N:20]=1.O.CN(C)[CH:33]=[O:34]>>[Cl:25][C:24]1[C:19]([O:34][CH2:33][C:9]([C:4]2[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=2)([O:14][CH3:15])[C:10]([NH:12][CH3:13])=[O:11])=[N:20][CH:21]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:23]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-hydroxymethyl-α-methoxy-N-methyl-phenylacetamide (1.00 g, 4.8 mmol) in N,N-dimethylformamide (5 ml) was stirred at 0° C., and 60% oily sodium hydride (0.19 g, 4.8 mmol) was added thereto. The mixture was stirred at 0° C. for 30 minutes, and then 2,3-dichloro-5-trifluoromethyl-pyridine (1.24 g, 5.7 mmol) was added. The mixture was stirred at 0° C. for 2 hours, and then ice and water were added in this order. The mixture was extracted with ether, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1) to give the desired compound (3-chloro-5-trifluoro-methyl-2-pyridyloxymethyl)-α-methoxy-N-methyl-phenylacetamide (1.40 g, 75%) as white crystals.
Workup
- stirringThe mixture was stirred at 0° C. for 2 hours
- extractionThe mixture was extracted with ether
- washwashed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated
- customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1)
Sources & evidence
- ORD record
- ord-eee2421ff0cd44eaa3899c16922066cb
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05948819
Reaction notes
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