Benzoyl Peroxide → 2-Bromomethyl-6-methoxybenzothiazole

HRID 1597783Notes

Reaction equation

HRID 1597783 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:19][C:20]1[S:21][C:22]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:23]=2[N:24]=1.[Br:31]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:19][C:20]1[S:21][C:22]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:23]=2[N:24]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 762546-Methoxy-2-methylbenzothiazole

Product 1

HCID 107063232-Bromomethyl-6-methoxybenzothiazoleYield 47%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

17.4 mg of dibenzoyl peroxide were added to a solution of 0.8 ml of 2-methyl-6-methoxybenzothiazole and 1.05 g of N-bromosuccinimide in 20 ml of carbon tetrachloride at room temperature and the resulting mixture was stirred under reflux for 5 hours. At the end of this time, the mixture was allowed to cool to room temperature and then extracted with methylene chloride. The resulting extract was washed consecutively with a saturated aqueous sodium sulfite solution, water and an aqueous sodium chloride solution and then dried over sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using an 8:1 by volume mixture of hexane and ethyl acetate, to give 649.3 mg (yield 47%) of the title compound as a solid having a melting point of 78° to 81° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. extractionextracted with methylene chloride
  3. extractionThe resulting extract
  4. washwas washed consecutively with a saturated aqueous sodium sulfite solution, water
  5. dry with materialan aqueous sodium chloride solution and then dried over sodium sulfate
  6. customThe solvent was then removed by evaporation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through silica gel using an 8:1
  8. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-ba53766c4c404ca48a6bc9e69b46e8d4
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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