Benzoyl Peroxide → HCID 22153312, compound

HRID 1111092Notes

Reaction equation

HRID 1111092 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=[O:4].[Br:23]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:22][C:2]([F:1])([F:21])[C:3]([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][Br:23])=[CH:16][CH:15]=1)=[O:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22153304HCID 22153304, compound

Product 1

HCID 22153312HCID 22153312, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A stirred solution of 213.0 g (0.7 mole) of 1-trifluoroacetyl-2-(4-methylphenyl)benzimidazole, 125.0 g (0.7 mole) of N-bromosuccinimide, and 3.39 g (2 mole %) of benzoyl peroxide in carbon tetrachloride is heated at reflux for 20 hours. After cooling to room temperature, the reaction is diluted by the addition of carbon tetrachloride, and the solid byproducts are removed by filtration. The filtrate is concentrated in vacuo, and the product is purified by recrystallization from tetrahydrofuran.

Workup

  1. temperatureat reflux for 20 hours
  2. customthe solid byproducts are removed by filtration
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe product is purified by recrystallization from tetrahydrofuran

Sources & evidence

ORD record
ord-f394ec07cba34c9ca24e82e7f5edeeeb
Source dataset
uspto-grants-1990_12
Patent number
US04978476

Reaction notes

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