Water → HCID 86591569, compound

HRID 1294215Notes

Reaction equation

HRID 1294215 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[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1.O.[CH3:28]N(C)C=O>>[CH3:28][CH:1]([NH: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)[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 12081Methyl 4-bromobenzoateHCID 24758Sodium hydrideHCID 824443N-methyl-4-phenyl-1,3-thiazol-2-amine

Product 1

HCID 86591569HCID 86591569, compoundYield 86%

Procedure

To a solution of 2-methylamino-4-phenylthiazole (1.76 g) in N,N-dimethylformamide (25 mL) was gradually added sodium hydride (60%, oil, 351 mg) at room temperature and the mixture was stirred for 30 min. Methyl 4-bromobenzoate (2.11 g) was added, and the mixture was further stirred for 1.5 hrs. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 4-[methyl(4-phenyl-2-thiazolyl)aminomethyl]benzoate (2.56 g, 86%) as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

Workup

  1. customat room temperature
  2. stirringthe mixture was further stirred for 1.5 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-12919b430bc04c0c92f68319b4ba9e79
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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