Benzylethanolamine → N-benzyl-6-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide
Reaction equation
[Br:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([F:11])[CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[CH2:17]([NH:24][CH2:25][CH2:26][OH:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>S(Cl)(Cl)=O.O1CCCC1.O>[CH2:17]([N:24]([CH2:25][CH2:26][OH:27])[C:8](=[O:10])[C:7]1[C:2]([Br:1])=[CH:3][CH:4]=[CH:5][C:6]=1[F:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 6-bromo-2-fluorobenzoic acid (10.0 g, 45.7 mmol) and N,N-dimethylformamide (0.100 ml) in thionylchloride (40 ml) was stirred at 85° C. for 12 hr, and the solvent was evaporated under reduced pressure. The residue was added to a solution of N-benzylethanolamine (6.91 g, 45.7 mmol) and triethylamine (9.55 ml, 68.6 mmol) in tetrahydrofuran (100 ml) under ice-cooling, and the mixture was stirred for 1 hr under ice-cooling and at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the desired product (15.7 g, 97.5%) as an oil.
Workup
- customthe solvent was evaporated under reduced pressure
- temperaturecooling
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b82cc26e824f49f7b8f03f60f8669ead
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247403B2
Reaction notes
Loading…