Acetic Acid → HCID 178463100, compound

HRID 1275454Notes

Reaction equation

HRID 1275454 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)S[CH2:16][CH2:15][C:14]3=[O:21])=[O:10])[CH:5]=[N:4]1)[CH3:2].OO.C(O)(=O)C.[S:28]([O-:31])(O)=[O:29].[Na+]>O>[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[S:28](=[O:31])(=[O:29])[CH2:16][CH2:15][C:14]3=[O:21])=[O:10])[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2×HCID 23665763Sodium BisulfiteHCID 178463099HCID 178463099, compound

Product 1

HCID 178463100HCID 178463100, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

1.0 Gram (3.31 mmol) of 6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-4-one and 0.83 g (7.28 mmol) of a 30 wt % hydrogen peroxide aqueous solution were added to 3 ml of glacial acetic acid, and then stirred under heat of 60° C. for 2.5 hours. While the reaction mixture was cooled in an ice bath after allowed to cool, a 1 wt % sodium hydrogensulfite aqueous solution was added to decompose excess hydrogen peroxide, and then the reaction mixture was diluted with water. A precipitated solid was extracted with ethyl acetate. An organic layer was washed with water and then with a saturated sodium chloride aqueous solution once, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 1.11 g (yield: quantitative) of the titled compound. Table 24 shows the physical property data of the titled compound.

Workup

  1. temperatureWhile the reaction mixture was cooled in an ice bath
  2. temperatureto cool
  3. extractionA precipitated solid was extracted with ethyl acetate
  4. washAn organic layer was washed with water
  5. dry with materialwith a saturated sodium chloride aqueous solution once, and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-736b2543bd0c4dad98cad401eeb6826f
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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