N-bromobutanimide → 3-(5-Bromomethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl ester

HRID 1265630Notes

Reaction equation

HRID 1265630 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12]([CH3:16])[S:13][C:14]=2[CH3:15])[CH:5]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12]([CH3:16])[S:13][C:14]=2[CH2:15][Br:18])[CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 696879213-(2,5-Dimethyl-thiazol-4-yl)-benzoic acid methyl ester

Product 1

HCID 696886923-(5-Bromomethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl esterYield 118.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-(2,5-dimethyl-thiazol-4-yl)-benzoic acid methyl ester (3.96 g), N-bromosuccinimid (3.13 g) and α,α′-bis(isobutyronitrile) (0.02 g) in CCl4 (60 mL) was heated at reflux for 30 min. The cooled mixture was filtered and the solvent was evaporated to give crude 3-(5-bromomethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl ester (6.2 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 min
  3. filtrationThe cooled mixture was filtered
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6958bfb5b006452fb2103f52cdaefc55
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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