Dichloromethane → HCID 23450698, compound

HRID 368957Notes

Reaction equation

HRID 368957 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([C:14]2[CH:15]=[N:16][N:17]([CH2:20][CH3:21])[C:18]=2[OH:19])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][S:7]2(=[O:23])=[O:22].ClCCl.C(=O)([O-])[O-].[K+].[K+].[CH2:33]([S:36](Cl)(=[O:38])=[O:37])[CH2:34][CH3:35]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:1][C:2]1[C:11]([C:12]([C:14]2[CH:15]=[N:16][N:17]([CH2:20][CH3:21])[C:18]=2[O:19][S:36]([CH2:33][CH2:34][CH3:35])(=[O:38])=[O:37])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][S:7]2(=[O:23])=[O:22]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 662791-Propanesulfonyl chlorideHCID 178463095HCID 178463095, compound

Product 1

HCID 23450698HCID 23450698, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A 30-ml eggplant type flask was charged with 0.30 g (0.86 mmol) of 5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide, 25 ml of dichloromethane, 5 ml of water and 0.14 g (0.86 mmol, 1 equivalent) of potassium carbonate. While the mixture was stirred at room temperature, 0.14 g (0.95 mmol, 1.1 equivalents) of n-propanesulfonyl chloride was dropwise added. 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 0.2 g of a crude product, and the crude product was recrystallized from ethanol to give 0.18 g (yield 48%) of 5-methyl-6-(1-ethyl-5-n-propanesulfonyloxypyrazole-4-yl)carbonylthiochroman-1,1-dioxide (Compound No. 58).

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 0.2 g of a crude product
  8. customthe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-d39e274aea7b4efb8efc055b0701bc2e
Source dataset
uspto-grants-2000_10
Patent number
US06136755

Reaction notes

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