Water → HCID 54332591, compound

HRID 343872Notes

Reaction equation

HRID 343872 reaction equation
[F:1][CH2:2][CH2:3][O:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH:17]=NN(CC)C=3O)[C:13]=2[CH3:15])[S:8](=[O:25])(=[O:24])[C:7](=C=O)[CH2:6]1.[NH:28]1[CH:32]=[CH:31][CH:30]=[N:29]1.[C:33](=[O:36])([O-])[O-].[K+].[K+].[CH2:39]([S:42](Cl)(=[O:44])=[O:43])[CH2:40][CH3:41].[OH2:46]>ClCCl.[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](=[CH:10][CH:11]=[C:12]([C:16]([C:17]3[CH:30]=[N:29][N:28]([CH2:32][CH3:31])[C:33]=3[O:36][S:42]([CH2:39][CH2:40][CH3:41])(=[O:44])=[O:43])=[O:46])[C:13]=2[CH3:15])[S:8](=[O:24])(=[O:25])[CH2:7][CH2:6]1

Participants

8

Reactant 5

HCID 962Water2×HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 662791-Propanesulfonyl chlorideHCID 178463045HCID 178463045, compound

Product 1

HCID 54332591HCID 54332591, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.63 Gram (1.6 mmol) of the 4-(2-fluoroethoxy)-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)-carbonylthiochroman-1,1-dioxide (corresponding to pyrazole derivative of the formula (Ia)) obtained in Preparation Example 5 was dissolved in 5 ml of dichloromethane. A solution of 0.4 g (3.2 mmol) of potassium carbonate as a base in 5 ml of water was added. To this mixture solution was added 0.4 ml (3.2 mmol) of n-propanesulfonyl chloride as a reaction reagent, and further, 0.05 g (0.2 mmol) of benzyltriethyl-ammonium chloride as a phase transfer catalyst was added. The mixture was allowed to react at room temperature for 1 day. After the completion of the reaction, 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 aqueous solution and with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel; hexane:ethyl acetate=1:1) to give 0.55 g (yield 68%) of the subject end product.

Workup

  1. customto react at room temperature for 1 day
  2. additionwere added
  3. customto separate the reaction mixture into two phases
  4. washThe resultant organic layer was consecutively washed with distilled water, with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by column chromatography (silica gel; hexane:ethyl acetate=1:1)
  8. customto give 0.55 g (yield 68%) of the subject end product

Sources & evidence

ORD record
ord-ce75c976910745e78d1c3f56e6f8d770
Source dataset
uspto-grants-1999_01
Patent number
US05863866

Reaction notes

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