HCID 54476646, compound → HCID 11189070, compound

HRID 1906848Notes

Reaction equation

HRID 1906848 reaction equation
C[N:2]([CH3:21])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([N:13]([CH3:20])[C:14]([CH:16]2[CH2:19][CH2:18][CH2:17]2)=[O:15])[CH:10]=[CH:11][CH:12]=1)=O.N[C:23]1[C:27]([C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=C[NH:25][N:24]=1>C(O)(=O)C>[C:28]([C:27]1[CH:23]=[N:24][N:25]2[C:5]([C:7]3[CH:8]=[C:9]([N:13]([CH3:20])[C:14]([CH:16]4[CH2:17][CH2:18][CH2:19]4)=[O:15])[CH:10]=[CH:11][CH:12]=3)=[CH:4][CH:3]=[N:2][C:21]=12)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 54476646HCID 54476646, compoundHCID 178509267HCID 178509267, compound

Product 1

HCID 11189070HCID 11189070, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reaction mixture comprising 2.86 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylcyclobutanecarboxamide, 1.88 g of 3-amino-4-benzoylpyrazole and 100 ml of glacial acetic acid was refluxed for 8 hours and then the solvent was removed in vacuo. The residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and then passed through a short pad of hydrous magnesium silicate. The addition of hexane to the refluxing eluate induced crystallization. After cooling, the desired product was collected, giving 3.05 g, mp 168°-170° C.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. additionThe addition of hexane
  5. customto the refluxing eluate induced crystallization
  6. temperatureAfter cooling
  7. customthe desired product was collected
  8. customgiving 3.05 g, mp 168°-170° C.

Sources & evidence

ORD record
ord-502ea903d83e4041b084fefa9bc5ae48
Source dataset
uspto-grants-1987_03
Patent number
US04654347

Reaction notes

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