Water → Methyl 4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzoate
Reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1.O>CN(C)C=O>[C:15]1([CH2:14][CH2:13][N:12]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)[C:9]2[S:10][CH:11]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-phenyl-N-(2-phenylethyl)-1,3-thiazole-2-amine (4.63 g, 16.5 mmol) in N,N-dimethylformamide (50 mL) was added 60% sodium hydride (990 mg, 24.8 mmol) and the mixture was stirred for 30 min. Methyl 4-(bromomethyl)benzoate (4.54 g, 19.8 mmol) was added and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (3.39 g, yield 48%) as a yellow oil.
Workup
- stirringthe mixture was stirred at room temperature for 2 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-99fc16c73d0747489d1d86b1172ba78b
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585880B2
Reaction notes
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