Benzil → 6-(1H-imidazol-1-ylmethyl)-2,3-diphenylquinoxaline

HRID 1086209Notes

Reaction equation

HRID 1086209 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([NH2:14])[C:10]([NH2:13])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:15]1([C:21](=O)[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]3[C:10](=[CH:11][CH:12]=2)[N:13]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:14]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 8651BenzilHCID 145184334-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine

Product 1

HCID 198759026-(1H-imidazol-1-ylmethyl)-2,3-diphenylquinoxalineYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.76 parts of 4-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine, 4.5 parts of diphenylethanedione and 80 parts of ethanol was stirred for 4 hours at reflux temperature. The reaction mixture was concentrated and the concentrate was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 1,1'-oxybisethane and ethanol. The product was filtered off and dried, yielding 4 parts (55%) of 6-(1H-imidazol-1-ylmethyl)-2,3-diphenylquinoxaline; mp. 159.3° C. (comp. 8).

Workup

  1. temperatureat reflux temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe concentrate was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from a mixture of 1,1'-oxybisethane and ethanol
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-667a741f17e24b979832b814cc6e4941
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

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