Ethyl 3-bromo-2-oxo-4-phenylbutanoate → Ethyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate

HRID 404832Notes

Reaction equation

HRID 404832 reaction equation
Br[CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:17][C:18]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:19]=1[C:20](=[S:22])[NH2:21]>CO>[CH2:10]([C:2]1[S:22][C:20]([C:19]2[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:18]=2[F:17])=[N:21][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 10755525Ethyl 3-bromo-2-oxo-4-phenylbutanoateHCID 227131172,5-Difluorothiobenzamide

Product 1

HCID 67451099Ethyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-bromo-2-oxo-4-phenylbutanoate (13.8 g, 48.4 mmol) in MeOH (161 mL) was slowly added 2,5-difluorobenzothioamide (8.38 g, 48.4 mmol) at room temperature. The reaction mixture was then refluxed for overnight. After cooled down, white precipitate was filtered, washed by cold ethanol and dried. A mixture of methyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate and ethyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate (10.5 g, 61%) was obtained as white solid. LC/MS (uplc): MW 346.1, 1.21 min for methyl ester; 360.1, 1.27 min for ethyl ester.

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was then refluxed for overnight
  3. temperatureAfter cooled down
  4. filtrationwhite precipitate was filtered
  5. washwashed by cold ethanol
  6. customdried
  7. additionA mixture of methyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate

Sources & evidence

ORD record
ord-ea35694fc8584dd3b93b056a23247954
Source dataset
uspto-grants-2014_06
Patent number
US08748626B2

Reaction notes

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