Water → HCID 67147049, compound

HRID 2422237Notes

Reaction equation

HRID 2422237 reaction equation
[CH3:1][NH:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[H-].[Na+].Br[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.O>CN(C)C=O>[CH3:1][N:2]([CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)[C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 824443N-methyl-4-phenyl-1,3-thiazol-2-amine

Product 1

HCID 67147049HCID 67147049, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-methyl-4-phenyl-1,3-thiazol-2-amine (1.67 g, 8.8 mmol) in N,N-dimethylformamide (25 mL) was added 60% sodium hydride (350 mg, 8.8 mmol), and the mixture was stirred for 30 min. Methyl 4-(bromomethyl)benzoate (2.1 g, 9.2 mmol) was added and the mixture was stirred at room temperature for 1.5 hrs. 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 (hexane/ethyl acetate=3:1) to give the title compound (2.6 g, yield 86%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hrs
  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 (hexane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-061371fcbb8748548d559e5fbe550b2b
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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