Azobisisobutyronitrile → HCID 68451721, compound

HRID 2220280Notes

Reaction equation

HRID 2220280 reaction equation
[CH3:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:11]([C:21]([F:24])([F:23])[F:22])[CH:10]=3)[S:8][C:4]=2[CH:3]=1.C1C(=O)N([Br:34])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:34][CH2:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[C:11]([C:21]([F:22])([F:23])[F:24])[CH:10]=3)[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 684537996-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1,3-benzothiazole

Product 1

HCID 68451721HCID 68451721, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 6-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)benzothiazole (120 mg, 0.325 mmol) in CCl4 (3.5 ml) is added NBS (64 mg, 1.1 eq.). The mixture is heated to reflux for 15 minutes before AIBN (5 mg, 0.1 eq.) is added. The reaction is refluxed overnight, filtered through celite and washed with CCl4. The filtrate is concentrated and purified by column chromatography (EtOAc/Hexane=9/95). 6-Bromomethyl-2-(2-trifluoromethyl-biphenyl-4-yl) benzothiazole (105 mg, 72%) is isolated.

Workup

  1. temperatureThe mixture is heated
  2. additionis added
  3. temperatureThe reaction is refluxed overnight
  4. filtrationfiltered through celite
  5. washwashed with CCl4
  6. concentrationThe filtrate is concentrated
  7. custompurified by column chromatography (EtOAc/Hexane=9/95)

Sources & evidence

ORD record
ord-fad97257e6ac453d91a0b6c4053b10b3
Source dataset
uspto-grants-2008_08
Patent number
US07417065B2

Reaction notes

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