Triethylamine → HCID 65479806, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(OCC)(=O)C>O1CCCC1>[Br:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:28])=[O:27])=[CH:24][CH:25]=1Participants
6
Procedure
To a solution of 2-(4-chlorophenyl)ethylamine (2.83 g) and triethylamine (1.46 ml) in tetrahydrofuran (50 ml), 4-(bromomethyl)benzenesulphonyl chloride (1.63 g) was added, and the mixed solution was stirred at room temperature for one hour. Ethyl acetate was added thereto, and the solution was washed with a saturated solution of ammonium chloride and then washed with water. The organic layer was dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate/n-hexane=10 to 30%) to give 4-(bromomethyl)-N-[2-(4-chlorophenyl)ethyl]benzene sulfonamide (2.04 g) as a colorless solid.
Workup
- washthe solution was washed with a saturated solution of ammonium chloride
- washwashed with water
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customevaporated under reduced pressure
- customto remove the solvent
- customThe resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate/n-hexane=10 to 30%)
Sources & evidence
- ORD record
- ord-41b2ebc3f58d40c8bf94820385acdf84
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461329B2
Reaction notes
Loading…