Acetic Acid → Thioxanthene, 10,10-dioxide

HRID 1935322

Reaction equation

HRID 1935322 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.OO.[OH2:17].C(O)(=[O:20])C>C(Cl)Cl>[O:17]=[S:6]1(=[O:20])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962Water2×HCID 67495Thioxanthene2×

Product 1

HCID 596953Thioxanthene, 10,10-dioxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Thioxanthene, 29 (2.9 g, 14.6 mmol) was dissolved in glacial acetic acid (90 mL). While under argon, the solution was treated with hydrogen peroxide (6.12 mL, 62.9 mmol of a 35% by wt water solution) and the reaction stirred at 100° C. for 1.5 hr. The reaction was cooled to room temperature, poured into water (250 mL), stirred 0.5 hrs and filtered to give a white solid. The solid was dissolved in CH2Cl2, washed with 5% sodium bisulfite (aq), dried over Na2SO4, filtered and concentrated to dryness in vacuo. Treatment of the resulting oil with methanol gave the title compound as a white solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. stirringstirred 0.5 hrs
  3. filtrationfiltered
  4. customto give a white solid
  5. washwashed with 5% sodium bisulfite (aq)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-9cc4e73a11a64dd0b7bc01f03e0e4bd8
Source dataset
uspto-grants-2002_05
Patent number
US06387893B1

Linked notes

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