Water → Methyl 4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzoate

HRID 507910Notes

Reaction equation

HRID 507910 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]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 543394-Phenyl-N-(2-phenylethyl)-2-thiazolamineHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 23111810Methyl 4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzoateYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 sodium hydride (60% in oil, 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 (5%-50% ethyl acetate/hexane) to give the title compound (3.39 g, yield 48%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (5%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-af6a9c70612f43b19eb5e9f02603a47f
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

Loading…