Azobisisobutyronitrile → 5-Bromo-4-(bromomethyl)-2-phenyl-1,3-thiazole

HRID 604683Notes

Reaction equation

HRID 604683 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH3:13].C1C(=O)N([Br:21])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][Br:21]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27954945-Bromo-4-methyl-2-phenyl-1,3-thiazole

Product 1

HCID 670577575-Bromo-4-(bromomethyl)-2-phenyl-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-Bromo-4-methyl-2-phenyl-1,3-thiazole (1.00 g, 3.93 mmol), NBS (0.84 g, 4.72 mmol) and catalytic amount of AIBN in CCl4 (20 mL) was heated at reflux for 24 h. No starting material was seen by 1H NMR. The solvent was removed. The title compound was obtained as a colorless solid after flash chromatography using EtOAc/hexane (3:97) as the eluant. 1H NMR (500 MHz, CDCl3): δ 7.90 (m, 3H), 7.48 (m, 2H), 4.61 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-466915342bb04b1bb10b725b02990c3b
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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