Benzoyl Peroxide → Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylate

HRID 1275876Notes

Reaction equation

HRID 1275876 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:11])[S:9][CH:10]=1)=[O:5])[CH3:2].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:12][CH2:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 11043146Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Methyl-4-thiazolecarboxylic acid ethyl ester (1 g) (Liebigs Ann. Chem. 1981, 623), N-bromosuccinimide (1.04 g) and a catalytic amount of benzoyl peroxide in chloroform (25 ml) was heated at reflux for 20 hours. After cooling, the reaction mixture was washed with saturated aqueous sodium bicarbonate, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 40% ethyl acetate in isohexane to give the product as an oil. Yield 0.5 g.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with 40% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-4362875e2d8d4b4fbdb89a614c12f7c4
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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