Water → HCID 67146541, compound

HRID 2422201Notes

Reaction equation

HRID 2422201 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][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][CH:22]=1.O>CN(C)C=O>[CH3:1][N:2]([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)[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 824443N-methyl-4-phenyl-1,3-thiazol-2-amineHCID 10064273HCID 10064273, compound

Product 1

HCID 67146541HCID 67146541, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of N-methyl-4-phenyl-2-thiazolamine (0.30 g, 1.7 mmol) in N,N-dimethylformamide (5 mL) was added 60% sodium hydride (72 mg, 1.8 mmol), and the mixture was stirred for 30 min. Ethyl 4-[(3-bromopropyl)oxy]benzenepropanoate (0.57 g, 1.8 mmol), was added, and the mixture was stirred at room temperature for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=15:1) to give the title compound (0.58 g, yield 80%). oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=15:1)

Sources & evidence

ORD record
ord-1c66238220094869a199f0da31a991e4
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

Loading…