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

HRID 1739460Notes

Reaction equation

HRID 1739460 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>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[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 2

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

Product 1

HCID 11043146Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylateYield 31.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of ethyl 2-methyl-4-thiazolecarboxylate [JCS 1946, 87, E. R. H. Jones, F. A. Robinson, M. N. Strachan] (5.0 g, 29.2 mmol) in CCl4 (30 ml) was treated with N-bromosuccinimide (5.2 g, 29.2 mmol) and benzoylperoxide (0.03 g). The reaction was heated to reflux while irradiating with a strong lamp for 21/2 hours. The reaction mixture was allowed to cool to ambient temperature, filtered and evaporated. The residue was purified by chromatography (eluant: CH2Cl2) to obtain ethyl 2-bromomethyl-4-thiazolecarboxylate (2.27 g, 31%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customwhile irradiating with a strong lamp for 21/2 hours
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (eluant: CH2Cl2)

Sources & evidence

ORD record
ord-0daef94f2fad4ab1baa8cbbccd101b4b
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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