Potassium Carbonate → HCID 178464082, compound

HRID 1031953Notes

Reaction equation

HRID 1031953 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-d6af03bdf2094ebe9f2f5d32fbc64127
Source dataset
uspto-grants-1990_09
Patent number
US04956378

Reaction notes

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