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

HRID 1601057Notes

Reaction equation

HRID 1601057 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.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[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 3

HCID 6547AzobisisobutyronitrileHCID 84462-MethylbenzothiazoleHCID 67184N-bromobutanimide

Product 1

HCID 27762582-(Bromomethyl)-1,3-benzothiazoleYield 72%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-methylbenzothiazole (2.0 g, 13.40 mmol), N-bromosuccinimide (2.39 g, 13.40 mmol), and AIBN (0.5 g, 3.04 mmol) in CCl4 (40 mL) was refluxed for 12 h, then the mixture was cooled and filtered. The filtrate was concentrated and purified by silica gel chromatography (5% EtOAc/hexane) to give the title compound (2.19 g, 72%) as a yellow oil: 1H NMR (250 MHz, DMSO-d6): δ 5.12 (s, 2H), 7.5 (m, 2H), 8.01 (dd, J=7.9, 1.8 Hz, 1H), 8.15 (dd, J=7.9, 1.8 Hz 1H).

Workup

  1. temperaturewas refluxed for 12 h
  2. temperaturethe mixture was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel chromatography (5% EtOAc/hexane)

Sources & evidence

ORD record
ord-df10a3eba44f4662b82eefbd8fd2c854
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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