N-bromobutanimide → 2-(Bromomethyl)-5-methoxy-1,3-benzothiazole

HRID 1179110Notes

Reaction equation

HRID 1179110 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:13]=2[N:14]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 76252Benzothiazole, 5-methoxy-2-methyl-

Product 1

HCID 534408462-(Bromomethyl)-5-methoxy-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2.58 g (14.5 mmol; 1.3 eq.) of N-bromosuccinimide and a spatula tip's worth of aza-bis-isobutyronitrile are added to 2 g (11.16 mmol) of 2-methyl-5-methoxy-1,3-benzothiazole in solution in 25 ml of anhydrous carbon tetrachloride. The reaction mixture is heated under reflux and under irradiation for 6 hours, with a spatula tip's worth of aza-bis-isobutyronitrile added every 2 hours. After returning to ambient temperature, the insoluble part formed is filtered, the solvent is evaporated off under reduced pressure and the residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane 1/4). The expected product is obtained in the form of a white solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. additionadded every 2 hours
  3. customAfter returning to ambient temperature
  4. customthe insoluble part formed
  5. filtrationis filtered
  6. customthe solvent is evaporated off under reduced pressure
  7. customthe residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane 1/4)

Sources & evidence

ORD record
ord-a9eefec36e21462688258f50332146a0
Source dataset
uspto-grants-2007_10
Patent number
US07279467B2

Reaction notes

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