Pyrazole → HCID 53932846, compound

HRID 343871Notes

Reaction equation

HRID 343871 reaction equation
[F:1][CH2:2][CH2:3][O:4][CH:5]1[C:14]2[C:9](=[C:10]([CH3:26])[CH:11]=[C:12]([C:16]([C:18]3[CH:19]=[N:20][N:21]([CH2:24][CH3:25])[C:22]=3[OH:23])=[O:17])[C:13]=2[CH3:15])[S:8](=[O:28])(=[O:27])[CH2:7][CH2:6]1.N1C=CC=N1.C(=O)([O-])[O-].[K+].[K+].[CH2:40]([S:43](Cl)(=[O:45])=[O:44])[CH2:41][CH3:42]>ClCCl.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[F:1][CH2:2][CH2:3][O:4][CH:5]1[C:14]2[C:9](=[C:10]([CH3:26])[CH:11]=[C:12]([C:16]([C:18]3[CH:19]=[N:20][N:21]([CH2:24][CH3:25])[C:22]=3[O:23][S:43]([CH2:40][CH2:41][CH3:42])(=[O:45])=[O:44])=[O:17])[C:13]=2[CH3:15])[S:8](=[O:28])(=[O:27])[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 662791-Propanesulfonyl chlorideHCID 178463105HCID 178463105, compound

Product 1

HCID 53932846HCID 53932846, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

1.00 Gram (2.44 mmol) of the 4-(2-fluoroethoxy)-5,8-dimethyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (corresponding to pyrazole derivative of the formula (Ia)) obtained in Preparation Example 1 was dissolved in 10 ml of dichloromethane. To this mixture solution was added a solution of 0.67 g (4.87 mmol) of potassium carbonate as a base in 10 ml of water. 0.42 Gram (2.93 mmol) of n-propanesulfonyl chloride (corresponding to compound of the formula (IV)) as a reaction reagent was added to the mixture, and 0.05 g (0.2 mmol) of benzyltriethylammonium chloride as a phase transfer catalyst was added. The mixture was allowed to react at room temperature for 2 hours, and then, further refluxed under heat for 2 hours. After the completion of the reaction, the reaction mixture was allowed to cool, and water and dichloromethane were added to separate the reaction mixture into two phases. The resultant organic layer was consecutively washed with distilled water, with a saturated sodium hydrogencarbonate and with a sodium chloride aqueous solution, dried over anhydrous sodium sulfate, concentrated and purified by flush column chromatography to give 0.79 g (yield 63%) of the subject end product.

Workup

  1. additionwas added
  2. customto react at room temperature for 2 hours
  3. temperaturefurther refluxed
  4. temperatureunder heat for 2 hours
  5. customAfter the completion of the reaction
  6. temperatureto cool
  7. customto separate the reaction mixture into two phases
  8. washThe resultant organic layer was consecutively washed with distilled water, with a saturated sodium hydrogencarbonate and with a sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. custompurified
  12. customby flush column chromatography
  13. customto give 0.79 g (yield 63%) of the subject end product

Sources & evidence

ORD record
ord-277d30a394e847978784297debf3fc08
Source dataset
uspto-grants-1999_01
Patent number
US05863866

Reaction notes

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