Water → HCID 88204903, compound

HRID 368958Notes

Reaction equation

HRID 368958 reaction equation
O.[C:2](=[O:5])([O-])[O-].[K+].[K+].[CH3:8][C:9]1[C:18]([C:19]([C:21]2C=[N:23][N:24]([CH2:27][CH3:28])[C:25]=2O)=[O:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][S:14]2(=[O:30])=[O:29].[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>ClCCl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:8][C:9]1[C:18]([C:19]([C:21]2[C:2]([O:5][S:37]([C:34]3[CH:35]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=3)(=[O:39])=[O:38])=[N:23][N:24]([CH2:27][CH3:28])[CH:25]=2)=[O:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][S:14]2(=[O:29])=[O:30]

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 178463095HCID 178463095, compound

Product 1

HCID 88204903HCID 88204903, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

5 ml of dichloromethane, 5 ml of water and 0.10 g (0.72 mmol, 1 equivalent) of potassium carbonate were added to 0.26 g (0.75 mmol) of 5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide in a 30-ml eggplant type flask. While the mixture was stirred at room temperature, a solution of 0.16 g (0.82 mmol, 1.1 equivalents) of p-toluenesulfonyl chloride in 1 ml of dichloromethane was dropwise added at room temperature. 5 mg of benzyltriethylammonium chloride (BTEAC) was added, and the mixture was allowed to react at the above temperature for 2 hours and then liquid-separated. An aqueous layer was extracted with dichloromethane. An organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The solvent was distilled off to give 0.24 g of a crude product, and the crude product was recrystallized from ethanol to give 0.14 g (yield 92%) of 5-methyl-6-(1-ethyl-p-toluenesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound No. 59).

Workup

  1. customto react at the above temperature for 2 hours
  2. customliquid-separated
  3. extractionAn aqueous layer was extracted with dichloromethane
  4. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off
  7. customto give 0.24 g of a crude product
  8. customthe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-11966fd6b51840488aebc0def141ee7c
Source dataset
uspto-grants-2000_10
Patent number
US06136755

Reaction notes

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