Formaldehyde → HCID 22097361, compound

HRID 1458995Notes

Reaction equation

HRID 1458995 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[C:11]([CH3:12])=[C:10]([C:13](=[O:15])[CH3:14])[CH:9]=[N:8]1.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.[ClH:29].[CH2:30](O)C.C=O>C(O)C>[ClH:29].[CH3:12][C:11]1[N:7]([C:2]2[N:1]=[CH:6][CH:5]=[CH:4][N:3]=2)[N:8]=[CH:9][C:10]=1[C:13](=[O:15])[CH2:14][CH2:30][N:26]1[CH2:27][CH2:28][N:23]([C:20]2[CH:19]=[CH:18][C:17]([OH:16])=[CH:22][CH:21]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 712Formaldehyde2×HCID 92467p-(1-Piperazinyl)phenolHCID 154563751-(2-Pyrimidinyl)-4-acetyl-5-methylpyrazoleHCID 21887872Ethanol hydrochloride

Product 1

HCID 22097361HCID 22097361, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.0 g of 1-(2-pyrimidinyl)-4-acetyl-5-methylpyrazole was dissolved in 50 ml of ethanol. After adding 2.6 g of 1-(4-hydroxyphenyl)piperazine, 10 ml of a 1N hydrochloric acid/ethanol solution and 1.6 g of paraformaldehyde, the mixture was heated under reflux for 24 hours. Further, 3.2 g of paraformaldehyde was added and the resulting mixture was heated under reflux for additional 48 hours. Then the reaction mixture was concentrated and neutralized by adding a saturated aqueous solution of sodium hydrogencarbonate. After extracting with chloroform, the extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue thus obtained was purified by silica gel column chromatography (chloroform:methanol=20:1), converted into hydrochloride by adding a 1N hydrochloric acid/ethanol solution and then recrystallized from ethanol. Thus 946 mg of the title compound was obtained in the form of a pale brown powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for additional 48 hours
  5. concentrationThen the reaction mixture was concentrated
  6. additionby adding a saturated aqueous solution of sodium hydrogencarbonate
  7. extractionAfter extracting with chloroform
  8. washthe extract was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. customAfter evaporating the solvent
  11. customthe residue thus obtained
  12. customwas purified by silica gel column chromatography (chloroform:methanol=20:1)
  13. additionby adding a 1N hydrochloric acid/ethanol solution
  14. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4ce94759cb5748dbb990820718daa350
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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