N-bromobutanimide → 5-(Bromomethyl)benzo[d]thiazole

HRID 2165077Notes

Reaction equation

HRID 2165077 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 143445645-Methyl-1,3-benzothiazole

Product 1

HCID 230437195-(Bromomethyl)benzo[d]thiazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-methylbenzothiazole (5.0 g), N-bromosuccinimide (6.0 g) and carbon tetrachloride (500 ml) was refluxed for 4 hours. Upon cooling, the mixture was evaporated to dryness and the residue chromatographed over silica gel. On elution with a mixture of methylene chloride and hexane (9:1), the title product was obtained as a white solid [0.56 g; NMR(CDCl3,60 MHz): 4.6 (s, 2H), 7.4 (dd, J=7 Hz, 2 Hz, 1H). 7.9 (d, J=7 Hz, 1H), 8.15 (d, J=2 Hz, 1H), 9.0 (s, 1H).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureUpon cooling
  3. customthe mixture was evaporated to dryness
  4. customthe residue chromatographed over silica gel
  5. washOn elution
  6. additionwith a mixture of methylene chloride and hexane (9:1)

Sources & evidence

ORD record
ord-1bc44546cc834138ac95aa6057598632
Source dataset
uspto-grants-1990_07
Patent number
US04939140

Reaction notes

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