Sodium hydride → HCID 69421658, compound
Reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](F)=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1>C1COCC1>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][C:18]=1[N+:23]([O-:25])=[O:24])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of (3-Hydroxy-propyl)-carbamic acid tert-butyl ester (11 mmoles, 1.88 ml) in THF (20 ml) was added to a suspension of sodium hydride 50% grade (23 mmoles, 1.058 g) in THF (20 ml) and stirred at 50° C for 1 hour. Following cooling to 0° C., 4-Chloro-1-fluoro-2-nitro-benzene was added and the mixture stirred at RT overnight. After quenching with water, the organic layer was separated and the aqueous layer was extracted several times with Ethyl acetate. The combined organic layers were washed with water then brine, and dried over sodium sulfate. The crude reaction was purified by flash chromatography to afford [3-(4-Chloro-2-nitro-phenoxy)-propyl]-carbamic acid tert-butyl ester.
Workup
- temperatureFollowing cooling to 0° C.
- stirringthe mixture stirred at RT overnight
- customAfter quenching with water
- customthe organic layer was separated
- extractionthe aqueous layer was extracted several times with Ethyl acetate
- washThe combined organic layers were washed with water
- dry with materialbrine, and dried over sodium sulfate
- customThe crude reaction
- customwas purified by flash chromatography
Sources & evidence
- ORD record
- ord-11f4048718404848b72634e30f0ea84b
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202244B2
Reaction notes
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