Azobisisobutyronitrile → 5-(Bromomethyl)-4-(4-chlorophenyl)-2-phenylthiazole

HRID 350710Notes

Reaction equation

HRID 350710 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:11][C:12]=2[CH3:13])=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:13][C:12]1[S:11][C:10]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 8036414Thiazole, 4-(4-chlorophenyl)-5-methyl-2-phenyl-

Product 1

HCID 230617605-(Bromomethyl)-4-(4-chlorophenyl)-2-phenylthiazoleYield 69%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-(4-chlorophenyl)-5-methyl-2-phenylthiazole (35.1 g), N-bromosuccinimide (24.0 g), azobisisobutyronitrile (4.11 g) and carbon tetrachloride (400 mL) was stirred with heating under reflux for 3 hrs. The precipitated solid was removed by filtration and the organic layer was concentrated. The residue was purified by silica gel column chromatography. 5-(Bromomethyl)-4-(4-chlorophenyl)-2-phenylthiazole (30.8 g, 69%) was obtained as crystals from a fraction eluted with hexane-ethyl acetate (19:1, volume ratio). Recrystallization from ethyl acetate gave colorless prism crystals. melting point: 108–109° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hrs
  3. customThe precipitated solid was removed by filtration
  4. concentrationthe organic layer was concentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2477b360099944448b6c292e855062fe
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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