2-Methylbenzothiazole → 2-(Bromomethyl)-1,3-benzothiazole

HRID 1597817Notes

Reaction equation

HRID 1597817 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:11][CH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 84462-MethylbenzothiazoleHCID 67184N-bromobutanimide

Product 1

HCID 27762582-(Bromomethyl)-1,3-benzothiazoleYield 68%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

476 mg of dibenzoyl peroxide were added to a solution of 5.87 g of 2-methylbenzothiazole and 15.4 g of N-bromosuccinimide in 60 ml of carbon tetrachloride at room temperature and the resulting mixture was stirred under reflux for 9 hours. At the end of this time, the reaction mixture was filtered and the resulting filtrate was concentrated by evaporation under reduced pressure to give a crude crystalline solid which was purified by column chromatography through silica gel using a 10:1 by volume mixture of hexane and ethyl acetate to give 6.10 g (yield 68%) of the title compound as a solid having a metling point of 43° to 45° C.

Workup

  1. temperatureunder reflux for 9 hours
  2. filtrationAt the end of this time, the reaction mixture was filtered
  3. concentrationthe resulting filtrate was concentrated by evaporation under reduced pressure
  4. customto give a crude crystalline solid which
  5. customwas purified by column chromatography through silica gel using a 10:1
  6. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-7bf0ec16a7a74cf883d89a07d60e5061
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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