N-bromobutanimide → HCID 68428806, compound

HRID 642342Notes

Reaction equation

HRID 642342 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[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:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[N:8][C:7]=1[CH2:19][Br:20])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 50997800Ethyl 4-Methyl-2-(3-methoxyphenyl)thiazole-5-carboxylate

Product 1

HCID 68428806HCID 68428806, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-(3-methoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (3.01 g, 10.88 mmole), N-bromosuccinimide (2.03 g, 11.42 mole) and benzoyl peroxide (132 mg, 0.54 mmole) in carbon tetrachloride (40 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 yellow solid (3.66 g). MS: (+) m/z 355.92, 357.92 (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-64e1479529ce4069bfd5fff726a5dea3
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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