Potassium Carbonate → HCID 178464082, compound

HRID 621596Notes

Reaction equation

HRID 621596 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:16]=2)=[CH:10][CH:9]=1.Cl.[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31]Cl)[CH3:28].[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39]>CN(C)C=O.O.CCOCC>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39].[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:16]=2)=[CH:12][CH:13]=1)[CH3:28]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 444972Fumaric AcidHCID 178516243HCID 178516243, compound

Product 1

HCID 178464082HCID 178464082, compoundYield 315.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (6.92 g), 4,5-dihydro-N-(4-hydroxyphenyl)-1-phenyl-1H-pyrazol-3-amine (4.22 g) and 2-diethylaminoethylchloride hydrochloride (2.95 g) in dimethylformamide (30 ml) were stirred together at room temperature for 25 hours. The reaction mixture was then diluted with water and extracted with ethyl acetate. The combined extracts were washed with water and dried. Solvent was removed to give an oil which was redissolved in ether and a solution of fumaric acid (0.33 g) in ether added to give a precipitate. This was collected and dried to give the title compound, (4.2 g) mp 54°-56° (dec).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. customdried
  4. customSolvent was removed
  5. customto give an oil which
  6. customto give a precipitate
  7. customThis was collected
  8. customdried

Sources & evidence

ORD record
ord-2e50a63f35e7429c83d4dff68ac50f6b
Source dataset
uspto-grants-1989_04
Patent number
US04824859

Reaction notes

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