Benzoyl Peroxide → HCID 19919354, compound

HRID 1648310Notes

Reaction equation

HRID 1648310 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([Cl:11])[N:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:15][O:14][C:12]([N:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH2:1][Br:16])[C:10]=2[N:9]=[C:8]1[Cl:11])=[O:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19919342HCID 19919342, compound

Product 1

HCID 19919354HCID 19919354, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 4-methyl-2-chloro-1H-benzimidazole-1-carboxylate (17.5 g, 0.078 mol), N-bromosuccinimide (13.9 g, 0.078 mol) and benzoyl peroxide (2.0 g) in carbon tetrachloride (175 mL) was stirred at reflux for 2 hours. The solution was cooled, filtered to remove succinimide by-products, evaporated and crystallized from ethyl acetate:hexane to give 17.1 g of methyl-4-(bromomethyl)-2-chloro-1H-benzimidazole-1-carboxylate as a pale yellow solid.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. customto remove succinimide by-products
  5. customevaporated
  6. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5f3e67b5868648b7a6c8a8e37440c1fb
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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