Dichloromethane → HCID 23450676, compound

HRID 368955Notes

Reaction equation

HRID 368955 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]([C:15]3[CH:16]=[N:17][N:18]([CH2:21][CH3:22])[C:19]=3[OH:20])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:25])(=[O:24])[CH2:4][CH2:3]1.ClCCl.C(=O)([O-])[O-].[K+].[K+].[CH2:35]([S:38](Cl)(=[O:40])=[O:39])[CH2:36][CH3:37]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:1][CH:2]1[C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]([C:15]3[CH:16]=[N:17][N:18]([CH2:21][CH3:22])[C:19]=3[O:20][S:38]([CH2:35][CH2:36][CH3:37])(=[O:40])=[O:39])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:25])(=[O:24])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 662791-Propanesulfonyl chlorideHCID 178463103HCID 178463103, compound

Product 1

HCID 23450676HCID 23450676, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A 30-ml eggplant type flask was charged with 0.25 g (0.69 mmol) of 4,5,8-trimethyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide, 5 ml of dichloromethane, 5 ml of water and 0.09 g (0.69 mmol, 1 equivalent) of potassium carbonate, and 0.11 g (0.76 mmol, 1.1 equivalents) of n-propanesulfonyl chloride was dropwise added with stirring 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 0.35 g of a crude product, which was recrystalized from ethanol to give 0.31 g (yield 95%) of 4,5,8-trimethyl-6-(1-ethyl-5-n-propanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound No. 51).

Workup

  1. additionwas dropwise added
  2. customto react at the above temperature for 2 hours
  3. customliquid-separated
  4. extractionAn aqueous layer was extracted with dichloromethane
  5. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto give 0.35 g of a crude product, which
  9. customwas recrystalized from ethanol

Sources & evidence

ORD record
ord-dc24f3751a6e483c8571e6b12f8543ec
Source dataset
uspto-grants-2000_10
Patent number
US06136755

Reaction notes

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