Potassium Carbonate → HCID 23450695, compound

HRID 368951Notes

Reaction equation

HRID 368951 reaction equation
[CH3:1][C:2]1([CH3:26])[C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]([C:15]3[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=3[OH:20])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:25])(=[O:24])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:33]([S:36](Cl)(=[O:38])=[O:37])[CH2:34][CH3:35]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:1][C:2]1([CH3:26])[C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]([C:15]3[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=3[O:20][S:36]([CH2:33][CH2:34][CH3:35])(=[O:38])=[O:37])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:25])(=[O:24])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 662791-Propanesulfonyl chlorideHCID 178426791HCID 178426791, compound

Product 1

HCID 23450695HCID 23450695, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

2.7 Grams (7.1 mmol) of the 4,4,5,8-tetramethyl-6-(1,3-dimethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide obtained in Preparation Example 6 was dissolved in 20 ml of methylene chloride, and a solution of 1.5 g of potassium carbonate in 20 ml of methylene chloride was added. Further, 0.76 g (10.5 mmol) of n-propanesulfonyl chloride was dissolved in 10 ml of methylene chloride, and the resultant solution was added. Then, 50 mg of benzyltriethylammonium chloride was added. The mixture was allowed to react at room temperature for 7 hours, and then a methylene chloride layer was separated. The methylene chloride layer was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. When the resultant oily substance was washed with an ethyl acetate/n-hexane mixed solvent (1:2 (v/v)) to form a solid, and the mixture was filtered to give 1.26 g (yield 74%) of 4,4,5,8-tetramethyl-6-(1,3-dimethyl-5-n-propanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound No. 30).

Workup

  1. customto react at room temperature for 7 hours
  2. customa methylene chloride layer was separated
  3. dry with materialThe methylene chloride layer was dried over sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. washWhen the resultant oily substance was washed with an ethyl acetate/n-hexane mixed solvent (1:2 (v/v))
  6. customto form a solid
  7. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-472d5bf6c2a04e848fbbc722655d8232
Source dataset
uspto-grants-2000_10
Patent number
US06136755

Reaction notes

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