4-Aminophenol → 4-(4-Hydroxyphenyl)thiomorpholine 1,1-Dioxide

HRID 235622Notes

Reaction equation

HRID 235622 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH:9]([S:11]([CH:14]=[CH2:15])(=[O:13])=[O:12])=[CH2:10]>C(O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[CH2:15][CH2:14][S:11](=[O:13])(=[O:12])[CH2:9][CH2:10]2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 6496Divinyl sulfone

Product 1

HCID 218452234-(4-Hydroxyphenyl)thiomorpholine 1,1-Dioxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 8.74 g of 4-aminophenol in 190 ml of ethanol is added dropwise at 50° to 11.34 g of divinyl sulfone, whereupon rinsing is carried out with 50 ml of ethanol and then the mixture is heated to boiling under reflux under argon for 3 hours. After cooling, the mixture is treated with 480 ml of water and stirred for 1 hour at 0°. The precipitated crystals are removed by filtration under suction, washed with 20 percent ethanol and water and dried. By recrystallization from dichloromethane/methanol/ether there is obtained 4-(p-hydroxyphenyl)-tetrahydro-4H-1,4-thiazine 1,1-dioxide of melting point 153°-155°.

Workup

  1. washwhereupon rinsing
  2. temperaturethe mixture is heated
  3. temperatureunder reflux under argon for 3 hours
  4. temperatureAfter cooling
  5. additionthe mixture is treated with 480 ml of water
  6. customThe precipitated crystals are removed by filtration under suction
  7. washwashed with 20 percent ethanol and water
  8. customdried
  9. customBy recrystallization from dichloromethane/methanol/ether there

Sources & evidence

ORD record
ord-32dc6ff0b5414e2aa765cbc1456fb3f3
Source dataset
uspto-grants-1987_02
Patent number
US04640918

Reaction notes

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