Sodium hydride → N-[2-(Benzyloxy)-4-bromo-6-nitrophenyl]-N-(2-methoxyethyl)acetamide
Reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([N+:18]([O-:20])=[O:19])[C:12]=1[NH:21][C:22](=[O:24])[CH3:23])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:26][CH2:27][O:28][CH3:29]>CN(C)C=O>[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([N+:18]([O-:20])=[O:19])[C:12]=1[N:21]([CH2:26][CH2:27][O:28][CH3:29])[C:22](=[O:24])[CH3:23])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of sodium hydride (60% dispersion in mineral oil, 1.78 g, 44.5 mmol) in N,N-dimethylformamide (100 mL) was added dropwise a solution of N-[2-(benzyloxy)-4-bromo-6-nitrophenyl]acetamide (13.5 g, 37.1 mmol, Step 1) in N,N-dimethylformamide at 0° C. over 10 minutes. After stirring at 0° C. for 20 minutes, 1-bromo-2-methoxyethane (7.21 g, 51.9 mmol) was added, and the mixture was stirred at 50° C. for 2 hours. After cooling to room temperature, the mixture was poured onto water, and the aqueous layer was extracted with ethyl acetate/toluene (3:1). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1) to afford the title compound as a gray solid (12.1 g, 77%).
Workup
- stirringthe mixture was stirred at 50° C. for 2 hours
- temperatureAfter cooling to room temperature
- additionthe mixture was poured onto water
- extractionthe aqueous layer was extracted with ethyl acetate/toluene (3:1)
- dry with materialThe combined organic layer was dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1)
Sources & evidence
- ORD record
- ord-2ffddae088974f23986f8611e078d108
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466166B2
Reaction notes
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