Potassium Carbonate → HCID 18522981, compound

HRID 1016248Notes

Reaction equation

HRID 1016248 reaction equation
[OH:1][C:2]1[N:6]([CH:7]2[CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([CH:22]=[CH2:23])[C:13]=1[O:24][CH3:25])=[O:11].O=S(Cl)Cl.[CH3:30]S(C1C=CC(C(O)=O)=C(OC)C=1C=C)(=O)=O.C1(N2C=CC(=O)N2)CC1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.COCCOC>[CH3:30][O:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9]2)[N:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([CH:22]=[CH2:23])[C:13]=1[O:24][CH3:25])=[O:11]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11184411HCID 11184411, compoundHCID 701529352137998-09-3HCID 178437382HCID 178437382, compound

Product 1

HCID 18522981HCID 18522981, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

5-Hydroxy-1-cyclopropyl-1H-pyrazol-4-yl-(4-methylsulfonyl-2-methoxy-3-vinylphenyl)methanone 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-cyclopropylpyrazolone (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-f5340d41512947a7a9bd22d1abee014a
Source dataset
uspto-grants-2002_11
Patent number
US06475957B1

Reaction notes

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