HCID 86741393, compound → HCID 86741392, compound

HRID 1906852Notes

Reaction equation

HRID 1906852 reaction equation
C[N:2]([CH3:22])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([N:13]([CH2:19][CH:20]=[CH2:21])[C:14](=[O:18])[O:15][CH2:16][CH3:17])[CH:10]=[CH:11][CH:12]=1)=O.NC1[C:28]([C:29]([C:31]2[O:32][CH:33]=[CH:34][CH:35]=2)=[O:30])=[CH:27][NH:26][N:25]=1>C(O)(=O)C>[O:32]1[CH:33]=[CH:34][CH:35]=[C:31]1[C:29]([C:28]1[CH:27]=[N:26][N:25]2[C:5]([C:7]3[CH:8]=[C:9]([N:13]([CH2:19][CH:20]=[CH2:21])[C:14](=[O:18])[O:15][CH2:16][CH3:17])[CH:10]=[CH:11][CH:12]=3)=[CH:4][CH:3]=[N:2][C:22]=12)=[O:30]

Participants

4

Reactant 2

HCID 86741393HCID 86741393, compoundHCID 178509268HCID 178509268, compound

Product 1

HCID 86741392HCID 86741392, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.01 mole of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-2-propenylcarbamic acid, ethyl ester and 0.01 mole of 3-amino-4-furoylpyrazole in 50 ml of glacial acetic acid is refluxed for 12 hours and the solvent removed in vacuo. The residue is partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer is separated, dried over anhydrous sodium sulfate and passed through a 2-3 cm thick layer of hydrous magnesium silicate. The filter cake is washed with 2-3 volumes of additional dichloromethane and the filtrate concentrated. Addition of hexane and concentration gives the desired product.

Workup

  1. temperatureis refluxed for 12 hours
  2. customthe solvent removed in vacuo
  3. customThe residue is partitioned between aqueous sodium bicarbonate and dichloromethane
  4. customThe organic layer is separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. washThe filter cake is washed with 2-3 volumes of additional dichloromethane
  7. concentrationthe filtrate concentrated
  8. additionAddition of hexane and concentration

Sources & evidence

ORD record
ord-d1fa2175f8c94bc09f9f341e136e4a06
Source dataset
uspto-grants-1987_03
Patent number
US04654347

Reaction notes

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