Acetic Acid → HCID 13607950, compound

HRID 236082Notes

Reaction equation

HRID 236082 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:10]2)=[CH:4][CH:3]=1.OO.[OH-:27].[Na+].C(O)(=[O:31])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)(=[O:17])=[O:16])[CH2:10]2)(=[O:31])=[O:27])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 13607947HCID 13607947, compound

Product 1

HCID 13607950HCID 13607950, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 37.96 g (0.10 mole) of 3-[(4-chlorophenyl)thio]-1-[(4-methylphenyl)sulfonyl]piperidine, 300 ml of glacial acetic acid, and 61.8 g of 30% hydrogen peroxide (0.6 mole) was stirred overnight at 90° C. The reaction mixture was cooled to room temperature and diluted with ice water. The diluted mixture was made alkaline with 50% aqueous sodium hydroxide and extracted with methylene chloride. The aqueous phase was discarded. The methylene chloride phase was washed with sodium sulfite to remove traces of peroxide. The methylene chloride solution was dried over magnesium sulfate, filtered and the solvent removed in vacuo to give a yellowish white solid. Recrystallization of an aliquot of the solid from methylene chloridehexanes gave the product, m.p. 186°-187° C. in 57.2% overall yield.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride phase was washed with sodium sulfite
  4. customto remove traces of peroxide
  5. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customto give a yellowish white solid
  9. customRecrystallization of an aliquot of the solid from methylene chloridehexanes
  10. customgave the product, m.p. 186°-187° C. in 57.2% overall yield

Sources & evidence

ORD record
ord-37d16adf1f2e4ffb8ba47d6a943bb93b
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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