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

HRID 901945Notes

Reaction equation

HRID 901945 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 11043146Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylateYield 44.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of ethyl 2-methylthiazole-4-carboxylate (5.0 g, 29 mmol), N-bromosuccinimide (6.2 g, 35 mmol) and azo-bis-(isobutyronitrile) (480 mg, 2.9 mmol) in carbon tetrachloride (150 ml) was heated at reflux for 18 h. The mixture was filtered and reduced. Chromatography (20% EtOAc/80% hexanes and 30% EtOAc/70% hexanes) afforded ethyl 2-bromomethylthiazole-4-carboxylate (3.25 g, 44%).

Workup

  1. temperatureat reflux for 18 h
  2. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-ad3b5e182c9d4f9ea387f5b6d5f0992f
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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