N-bromobutanimide → Ethyl 2-bromo-4-(bromomethyl)thiazole-5-carboxylate

HRID 642324Notes

Reaction equation

HRID 642324 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([Br:11])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].[Br:13]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]([Br:11])=[N:8][C:7]=1[CH2:12][Br:13])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 68428140Ethyl 2-bromo-4-(bromomethyl)thiazole-5-carboxylateYield 59.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-Bromo-4-methyl-thiazole-5-carboxylic acid ethyl ester (5.67 g, 22.68 mmol), N-bromosuccinimide (4.44 g, 24.95 mmol) and benzoyl peroxide (275 mg, 1.13 mmol) in carbon tetrachloride (25 mL) was refluxed for 16 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 white solid (4.46 g): MS: (+) m/z 337.80, 329.93, 331.93 (M+1, 79Br/81Br).

Workup

  1. temperaturewas refluxed for 16 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-3e84403aeb044e36891e23b048abaf59
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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