N-bromobutanimide → 4-Bromomethyl-2-phenyl-benzothiazole

HRID 1589848Notes

Reaction equation

HRID 1589848 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:17][CH2:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 12349092HCID 12349092, compound

Product 1

HCID 156764834-Bromomethyl-2-phenyl-benzothiazole

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

42.8 g (190 mmol) of 4-methyl-2-phenyl-benzothiazole [compare Perregaard, Lawesson, Acta Chem. Scand. Ser. B, 31, 203 (1977)] were dissolved in 1 l of carbon tetrachloride, and catalytic amounts of 2,2'-azoisobutyronitrile were added. 40.6 g (0.228 mol) of N-bromosuccinimide (NBS) were were added under reflux in portions and the mixture was boiled overnight. A further 40.6 g of NBS were added and the mixture was boiled for 2 h. After cooling, the mixture was diluted with methylene chloride, washed with water, dried and concentrated, and the residue was crystallized using petroleum ether.

Workup

  1. temperatureunder reflux in portions
  2. waitthe mixture was boiled for 2 h
  3. temperatureAfter cooling
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was crystallized

Sources & evidence

ORD record
ord-0585b9fec3374e09942c6f3a79840291
Source dataset
uspto-grants-1993_04
Patent number
US05200420

Reaction notes

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