Acetic Acid → HCID 53771494, compound

HRID 1886359Notes

Reaction equation

HRID 1886359 reaction equation
[Cl: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.C(O)(=O)C.[CH3:26][CH:27]([CH3:36])[CH2:28][C:29](=O)[C:30](OCC)=[O:31].[OH-].[Na+]>O>[Cl: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)[NH:15][C:30](=[O:31])[C:29]([CH2:28][CH:27]([CH3:36])[CH3:26])=[N:16]3)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 117716Ethyl 4-methyl-2-oxovalerateHCID 14500563HCID 14500563, compound

Product 1

HCID 53771494HCID 53771494, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred and cooled (0° C.) solution of 9.1 parts of 4-[(3-chlorophenyl)(1H-imidazol-1-yl)methyl]-1,2-benzenediamine in 80 parts of acetic acid and 20 parts of water were added portionwise 5.8 parts of ethyl 4-methyl-2-oxopentanoate. Upon completion, stirring was continued for 4 hours at room temperature. The reaction mixture was poured into 100 parts of water and the whole was neutralized with a sodium hydroxide solution 3N. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane 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 2-propanone and 1,1'-oxybisethane. The product was filtered off (the filtrate was set aside) and dried, yielding 1.5 parts (12.6%) of 6-[(3-chlorophenyl) (1H-imidazol-1-yl)methyl]-3-(2-methylpropyl)-2(1H)-quinoxalinone; mp. 209.7° C. (comp. 178)

Workup

  1. stirringUpon completion, stirring
  2. extractionThe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of dichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane
  11. filtrationThe product was filtered off (the filtrate
  12. customdried

Sources & evidence

ORD record
ord-ad94a749cdd344edbb8d2896e4fd09ee
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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