N-bromobutanimide → Ethyl 4-(bromomethyl)-2-phenyl-1,3-thiazole-5-carboxylate

HRID 2407709Notes

Reaction equation

HRID 2407709 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH2:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2743970Ethyl 4-methyl-2-phenyl-1,3-thiazole-5-carboxylate

Product 1

HCID 12736369Ethyl 4-(bromomethyl)-2-phenyl-1,3-thiazole-5-carboxylateYield 100.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 4-methyl-2-phenylthiazole-5-carboxylate (5.00 g), N-bromosuccinimide (3.78 g) and benzoyl peroxide (0.49 g) were suspended in carbon tetrachloride (50 mL) and heated at reflux overnight. The reaction mixture was cooled to room temperature and partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The combined organics were dried over magnesium sulfate and concentrated under reduced pressure to afford the crude title compound (6.60 g), which was used without further purification possessing the following physical data.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-28f09c425f3d43fabfdcea9eb508e1f1
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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