N-bromobutanimide → 4-Bromomethyl-2-(4-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 642294

Reaction equation

HRID 642294 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:19])=[O:5])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH2:19][Br:20])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 7540952Ethyl 2-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 684274184-Bromomethyl-2-(4-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 94.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-(4-Methoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (1.41 g, 5.09 mmol), N-bromosuccinimide (951 mg, 5.34 mmol) and benzoyl peroxide (62 mg, 0.25 mmol) in carbon tetrachloride (20 mL) was refluxed for 15 h before it was cooled to room temperature and partitioned between dichloromethane and water, the organic layer was washed with saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (1.71 g): MS: (+) m/z 355.96, 357.96 (M+1, 79Br/81Br).

Workup

  1. temperaturewas refluxed for 15 h before it
  2. custompartitioned between dichloromethane and water
  3. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-084115644596457d9a8a75ade597e29d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Linked notes

Loading…