Water → Thioxanthene

HRID 1836839Notes

Reaction equation

HRID 1836839 reaction equation
[CH:1]1[C:14]2[C:13](=O)[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.[OH-].[K+].O.NN.O>C(O)CO>[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

Participants

6

Reactant 4

HCID 962WaterHCID 10295ThioxanthoneHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 67495ThioxantheneYield 61.2%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
140 °C

Procedure

Thioxanthone (0.21 g) was dissolved in ethylene glycol (1.5 ml). Potassium hydroxide (0.19 g) and hydrazine monohydrate (0.15 ml) were added to the solution. The mixture was heated at 140° C. with stirring for 2 hr and then at 200° C. for 4 hr. The temperature of the reaction solution was returned to room temperature. Water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgSO4. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform) to give thioxanthene (0.12 g).

Workup

  1. waitat 200° C. for 4 hr
  2. customwas returned to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous MgSO4
  5. customThe solvent was then removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform)

Sources & evidence

ORD record
ord-050eb66b98e04ea28b52ad56b9b6b5cc
Source dataset
uspto-grants-2004_08
Patent number
US06777414B1

Reaction notes

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