HCID 54370975, compound → HCID 11450003, compound

HRID 1248801Notes

Reaction equation

HRID 1248801 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][NH:4][N:3]=1.CN(C)[CH:11]=[CH:12][C:13]([C:15]1[CH:16]=[C:17]([N:21]([CH2:26][CH3:27])[C:22](=[O:25])[CH2:23][CH3:24])[CH:18]=[CH:19][CH:20]=1)=O>C(O)(=O)C>[C:7]([C:6]1[CH:5]=[N:4][N:3]2[C:13]([C:15]3[CH:16]=[C:17]([N:21]([CH2:26][CH3:27])[C:22](=[O:25])[CH2:23][CH3:24])[CH:18]=[CH:19][CH:20]=3)=[CH:12][CH:11]=[N:1][C:2]=12)#[N:8]

Participants

4

Reactant 2

HCID 54370975HCID 54370975, compoundHCID 178510443HCID 178510443, compound

Product 1

HCID 11450003HCID 11450003, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.54 g of 3-amino-4-pyrazolecarbonitrile and 1.37 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethylpropanamide in 50 ml of glacial acetic acid was refluxed for 8 hours and then the solvent was removed. The residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic layer was separated, dried, passed through a pad of hydrous magnesium silicate and hexane was added to the refluxing filtrate. The mixture was then cooled and the solid collected, giving 1.3 g of the desired product, mp 161°-162° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customthe solvent was removed
  3. customThe residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  4. customThe organic layer was separated
  5. customdried
  6. additionwas added to the refluxing filtrate
  7. temperatureThe mixture was then cooled
  8. customthe solid collected

Sources & evidence

ORD record
ord-458b8dc32d3f482bbaf69a7865c07934
Source dataset
uspto-grants-1986_12
Patent number
US04626538

Reaction notes

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