Benzoyl Peroxide → 2-(Benzothiazol-2-yl)-5-bromomethylpyridine

HRID 224312Notes

Reaction equation

HRID 224312 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1.[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][Br:17])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 123541122-(5-Methylpyridin-2-yl)-1,3-benzothiazole

Product 1

HCID 233325222-(Benzothiazol-2-yl)-5-bromomethylpyridineYield 70.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In 800 ml of dry carbon tetrachloride was dissolved 20 g (0.088 mol) of 2-(benzothiazol-2-yl)-5-methylpyridine, followed by the addition of 16.4 g (0.092 mol) of N-bromosuccinimide and a catalytic amount of benzoyl peroxide. The mixture was heated at reflex for 10 hours, after which time it was allowed to cool down to room temperature. The precipitated succinimide was filtered off, the filtrate concentrated to 200 ml and the resulting crude crystals collected by filtration. Yield 24 g. Recrystallization from ligroine yielded 19 g of 2-(benzothiazol-2-yl)-5-bromomethylpyridine as colorless needles.

Workup

  1. temperatureThe mixture was heated at reflex for 10 hours
  2. filtrationThe precipitated succinimide was filtered off
  3. concentrationthe filtrate concentrated to 200 ml
  4. filtrationthe resulting crude crystals collected by filtration
  5. customRecrystallization from ligroine

Sources & evidence

ORD record
ord-f7b9a032c1a341a09da80ded2ed885f8
Source dataset
uspto-grants-1980_11
Patent number
US04232010

Reaction notes

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