1-Phenyl-2-(4-methoxyphenyl)benzimidazole → HCID 135601299, compound

HRID 378390Notes

Reaction equation

HRID 378390 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Br.C(O)(=O)C>[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 193539961-Phenyl-2-(4-methoxyphenyl)benzimidazole

Product 1

HCID 135601299HCID 135601299, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 1-phenyl-2-(4-methoxyphenyl)benzimidazole(0.60 g, 2.0 mmol) in hydrobromic acid (6 ml) and acetic acid (6 ml) was refluxed for 40 hours. The reaction mixture was extracted with diethyl ether (5×150 ml) at a pH of 3-5. The organic solvents were discarded. The aqueous phase was alkalinized to pH 8-9 and extracted with ethyl acetate (5×150 ml). The organic fractions were combined and dried over potassium carbonate, then filtered and the solvents were removed in vacuo to yield a white solid. The solid was triturated in diethyl ether and filtered to yield 0.25 grams of the desired product.

Workup

  1. extractionThe reaction mixture was extracted with diethyl ether (5×150 ml) at a pH of 3-5
  2. extractionextracted with ethyl acetate (5×150 ml)
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. customthe solvents were removed in vacuo
  6. customto yield a white solid
  7. customThe solid was triturated in diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-0395deeaac3849029805414ab1b83a78
Source dataset
uspto-grants-2000_02
Patent number
US06030992

Reaction notes

Loading…