Potassium Carbonate → HCID 18522981, compound

HRID 413017Notes

Reaction equation

HRID 413017 reaction equation
O=S(Cl)Cl.[CH3:5][S:6]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[C:11]([O:18][CH3:19])[C:10]=1[CH:20]=[CH2:21])(=[O:8])=[O:7].[CH:22]([N:25]1[CH:29]=[CH:28][C:27](=O)[NH:26]1)([CH3:24])[CH3:23].[C:31]([O-])([O-])=[O:32].[K+].[K+]>C1(C)C=CC=CC=1.COCCOC>[CH3:31][O:32][C:29]1[N:25]([CH:22]2[CH2:24][CH2:23]2)[N:26]=[CH:27][C:28]=1[C:13]([C:12]1[CH:16]=[CH:17][C:9]([S:6]([CH3:5])(=[O:7])=[O:8])=[C:10]([CH:20]=[CH2:21])[C:11]=1[O:18][CH3:19])=[O:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 11184411HCID 11184411, compoundHCID 229186161-(Propan-2-yl)-1,2-dihydro-3H-pyrazol-3-one

Product 1

HCID 18522981HCID 18522981, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

SOCl2 (1.2 g, 10 mmol) was added to a solution of 4-methylsulfonyl-2-methoxy-3-vinylbenzoic acid (1.6 g, 6 mmol) in toluene (60 ml) and the mixture was heated at reflux for 2 h. The mixture was then concentrated and the product was added to a solution of N-isopropylpyrazolone (6 mmol), K2CO3 (1.6 g, 11.6 mmol) in DME (30 ml) and the mixture was stirred at RT overnight. The mixture was subsequently heated at reflux for 2 h and concentrated and the residue was dissolved in H2O. The H2O phase was extracted 3× with CH2Cl2, and the combined organic phases were dried over MgSO4 and concentrated.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationThe mixture was then concentrated
  4. temperatureThe mixture was subsequently heated
  5. temperatureat reflux for 2 h
  6. concentrationconcentrated
  7. dissolutionthe residue was dissolved in H2O
  8. extractionThe H2O phase was extracted 3× with CH2Cl2
  9. dry with materialthe combined organic phases were dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d56ca350bbfe4fb4950b64ed48ed9668
Source dataset
uspto-grants-2003_05
Patent number
US06566307B1

Reaction notes

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