Benzoyl Peroxide → 3-(Bromomethyl)isothiazolo[5,4-b]pyridine

HRID 424642Notes

Reaction equation

HRID 424642 reaction equation
[Br:1]NC(=O)CCC(N)=O.[CH3:10][C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][N:12]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:10][C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][N:12]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 124969753-Methyl[1,2]thiazolo[5,4-b]pyridine

Product 1

HCID 667026993-(Bromomethyl)isothiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinamide (10.7 mmol) was added to a solution of 3-methylisothiazolo[5,4-b]pyridine (10.0 mmol) in carbontetrachloride (20 mL). Benzoyl peroxide (0.82 mmol) was added and the reaction mixture was heated at reflux for 48 h. The reaction mixture was filtered through Celite (ethyl acetate) and the eluent was concentrated to provide crude 3-(bromomethyl)isothiazolo[5,4-b]pyridine as a yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. filtrationThe reaction mixture was filtered through Celite (ethyl acetate)
  4. concentrationthe eluent was concentrated

Sources & evidence

ORD record
ord-b478c96bbd39448c9af2860e121b0708
Source dataset
uspto-grants-2012_01
Patent number
US08106066B2

Reaction notes

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