Acetic Acid → HCID 13476015, compound

HRID 1247976Notes

Reaction equation

HRID 1247976 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)=[CH:5][NH:4][N:3]=1.CN(C)[CH:14]=[CH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:28])[C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=1)=O.[C:30](O)(=[O:32])C>>[O:32]1[CH:30]=[CH:9][CH:10]=[C:11]1[C:7]([C:6]1[CH:5]=[N:4][N:3]2[C:16]([C:18]3[CH:23]=[CH:22][C:21]([N:24]([CH3:28])[C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)=[CH:15][CH:14]=[N:1][C:2]=12)=[O:8]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 54238762HCID 54238762, compoundHCID 178509257HCID 178509257, compound

Product 1

HCID 13476015HCID 13476015, compound

Procedure

A solution of 1.77 g of 3-amino-4-furanylpyrazole and 2.46 g of N-[4-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide in 50 ml of glacial acetic acid was refluxed for 8 hours. Evaporation of the reaction mixture gave a gum which was partitioned between an aqueous saturated sodium bicarbonate solution and methylene chloride. The methylene chloride extract was dried and passed through a short column of hydrous magnesium silicate adsorbent. The eluate was refluxed on a steam bath with gradual addition of hexane until turbidity. On cooling, the desired compound was collected by filtration, mp 202°-204° C.

Workup

  1. customEvaporation of the reaction mixture
  2. customgave a gum which
  3. customwas partitioned between an aqueous saturated sodium bicarbonate solution and methylene chloride
  4. extractionThe methylene chloride extract
  5. customwas dried
  6. temperatureThe eluate was refluxed on a steam bath with gradual addition of hexane until turbidity
  7. temperatureOn cooling
  8. filtrationthe desired compound was collected by filtration, mp 202°-204° C.

Sources & evidence

ORD record
ord-c3c7a56d51374e98a8a4f2fb26c5bacd
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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