Glyoxal → HCID 19875882, compound

HRID 1886357Notes

Reaction equation

HRID 1886357 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[C:9]2[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[CH:22](=O)[CH:23]=O>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[C:9]2[CH:10]=[C:11]3[C:12](=[CH:13][CH:14]=2)[N:15]=[CH:23][CH:22]=[N:16]3)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 19875856HCID 19875856, compound

Product 1

HCID 19875882HCID 19875882, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 8.1 parts of 4-[(3-fluorophenyl)(1H-imidazol-1-yl)methyl]-1,2-benzenediamine, 5 parts of ethanedial and 80 parts of methanol was stirred at reflux temperature. Upon complete reaction, the mixture was evaporated to dry and the residue was taken up in water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) was eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 6.35 parts (74.5%) of 6-[(3-fluorophenyl)(1H-imidazol-1-yl)methyl]quinoxaline; mp. 109.7° C. (comp. 15).

Workup

  1. temperatureat reflux temperature
  2. customUpon complete reaction
  3. customthe mixture was evaporated
  4. customto dry
  5. extractionThe product was extracted with trichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of dichloromethane and methanol (98:2 by volume)
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customThe residue was crystallized from 2,2'-oxybispropane
  14. filtrationThe product was filtered off
  15. customdried

Sources & evidence

ORD record
ord-dfffbb70e0a244438287d8dcc4307abf
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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