Acetic Acid → HCID 178519496, compound

HRID 1723160Notes

Reaction equation

HRID 1723160 reaction equation
[N:1]1([CH:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]2[CH:23]=[CH:22][C:10]3[NH:11][C:12]([CH:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[OH:15])=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].C(O)(=O)C.[OH-].[NH4+]>O>[N:1]1([CH:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]2[CH:23]=[CH:22][C:10]3[NH:11][C:12]([C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[O:15])=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 24502Potassium DichromateHCID 178519497HCID 178519497, compound

Product 1

HCID 178519496HCID 178519496, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.5 parts of 5-[(1H-imidazol-1-yl)phenylmethyl]-α-phenyl-1H-benzimidazole-2-methanol, 1.4 parts of potassium dichromate and 25 parts of acetic acid was stirred for 45 minutes at room temperature. Water was added to the mixture and the whole was made alkaline with concentrated ammonium hydroxide. The product was extracted with a mixture of trichloromethane and methanol (95:5 by volume). The extract was dried, filtered and evaporated. The residue was purified twice by column chromatography over silica gel using a mixture of trichloromethane, methanol and methanol, saturated with ammonia (90:5:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 63 parts of ethyl acetate. The product was filtered off and dried in vacuo at 100° C. during 17 hours, yielding 0.8 parts (54%) of [5-[(1H-imidazol-1-yl)phenylmethyl]-1H-benzimidazol-2-yl] phenylmethanone; mp. 223.3° C. (compound 264).

Workup

  1. extractionThe product was extracted with a mixture of trichloromethane and methanol (95:5 by volume)
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified twice by column chromatography over silica gel using
  6. additiona mixture of trichloromethane, methanol and methanol
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 63 parts of ethyl acetate
  10. filtrationThe product was filtered off
  11. customdried in vacuo at 100° C. during 17 hours

Sources & evidence

ORD record
ord-576d9a9036194cd988a84747ab6c5f2c
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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