Acetic Acid → 4-(4-Hydroxyphenyl)thiomorpholine 1,1-Dioxide

HRID 369561Notes

Reaction equation

HRID 369561 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)(=O)C>C(O)C>[O:12]=[S:11]1(=[O:13])[CH2:14][CH2:15][N:1]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4034-AminophenolHCID 6496Divinyl sulfone

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The preparation of stabilizer compounds of formula S of the invention is illustrated by the following synthesis of Stabilizer S-3. ##STR16## A mixture of para-aminophenol (25 g, 229 mmol) and divinylsulfone (32.5 g, 275 mmol) was heated at reflux in ethanol (100 ml) for two days. The reaction mixture was cooled and poured into ice water (1 l). The mixture was made acidic with the addition of acetic acid and the resulting tan solid was isolated by filtration and washed with water. Recrystallization from methanol afforded the desired 4-(1',1'-dioxothiomorpholino)phenol as a light tan crystalline solid (35 g, 67%). Mp. 149-151° C.

Workup

  1. customThe preparation of stabilizer compounds of formula S of the invention
  2. customis illustrated by the following synthesis of Stabilizer S-3
  3. temperaturewas heated
  4. temperatureThe reaction mixture was cooled
  5. customthe resulting tan solid was isolated by filtration
  6. washwashed with water
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-2bdd4eec61004444b009636ccb725bf5
Source dataset
uspto-grants-2000_10
Patent number
US06140031

Reaction notes

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