Benzylethanolamine → HCID 60740620, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.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:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
Procedure
A solution of 5-bromo-2-fluorobenzoic acid (3.00 g, 13.7 mmol) and N,N-dimethylformamide (0.100 ml) in thionylchloride (20 ml) was stirred at 85° C. for 2 hr, and the solvent was evaporated under reduced pressure. The residue was added under ice-cooling to a solution of N-benzylethanolamine (2.07 g, 13.7 mmol) and triethylamine (2.87 ml, 20.6 mmol) in tetrahydrofuran (30 ml), and the mixture was stirred under ice-cooling for 1 hr and at room temperature for 12 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 (4.75 g, 98.3%) as an oil.
Workup
- customthe solvent was evaporated under reduced pressure
- additionThe residue was added under ice-
- 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-0283bc1f4b6b4a0098ed6927af8f74db
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247403B2
Reaction notes
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