Acetic Acid → HCID 13476010, compound

HRID 1247975Notes

Reaction equation

HRID 1247975 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:19]=[C:20]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])[CH:21]=[CH:22][CH:23]=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:19]=[C:20]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)=[CH:15][CH:14]=[N:1][C:2]=12)=[O:8]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 54179722HCID 54179722, compoundHCID 178509257HCID 178509257, compound

Product 1

HCID 13476010HCID 13476010, compound

Procedure

A solution of 1.77 g 3-amino-4-furanylpyrazole and 2.46 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]propanamide in 50 ml of glacial acetic acid was refluxed for 8 hours. Removal of all solvents gave a gum which was partitioned between an aqueous saturated sodium bicarbonate solution and methylene chloride. The methylene chloride extract was dried with powdered anhydrous sodium sulfate and then passed through a short column of a hydrous magnesium silicate adsorbent. The eluate was refluxed on a steam bath with gradual addition of hexanes until turbidity was noted. The desired product was collected by filtration of the cooled crystallization mixture, (2.05 g, mp 185°-186° C.).

Workup

  1. customRemoval of all solvents
  2. customgave a gum which
  3. customwas partitioned between an aqueous saturated sodium bicarbonate solution and methylene chloride
  4. extractionThe methylene chloride extract
  5. dry with materialwas dried with powdered anhydrous sodium sulfate
  6. temperatureThe eluate was refluxed on a steam bath with gradual addition of hexanes until turbidity
  7. filtrationThe desired product was collected by filtration of the cooled crystallization mixture, (2.05 g, mp 185°-186° C.)

Sources & evidence

ORD record
ord-c461fbb176e4406698c2111608d265bd
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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