Phenol → HCID 20218064, compound

HRID 236098Notes

Reaction equation

HRID 236098 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][N:13]2S(C2C=CC=CC=2)(=O)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(O)C=CC=CC=1>Br>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 13607970HCID 13607970, compound

Product 1

HCID 20218064HCID 20218064, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 45.1 g (0.109 mole) of 2-[[(4-chlorophenyl)sulfonyl]methyl]-1-phenylsulfonylpiperidine and 200 ml of phenol in 200 ml of 48% hydrobromic acid was refluxed for 1 hr. The reaction mixture was quenched in water and 50% sodium hydroxide was added until the solution was basic (pH>10). The mixture was extracted with methylene chloride. The methylene chloride phase was separated, extracted with dilute aqueous sodium hydroxide followed by several portions of dilute sulfuric acid. The acidic phase was separated, basified with solid sodium carbonate and extracted with methylene chloride. This methylene chloride solution was dried over sodium sulfate and evaporated to remove solvent in vacuo to give an oil, the free base of the title compound. The free base was dissolved in methanol and converted to the hydrochloride salt with ethereal hydrogen chloride and the salt was recrystallized from methanol-diethyl ether to give 22.82 g (67.5%) white crystalline solid, m.p. 223.5°-224.5° C.

Workup

  1. temperaturewas refluxed for 1 hr
  2. customThe reaction mixture was quenched in water
  3. addition50% sodium hydroxide was added until the solution
  4. extractionThe mixture was extracted with methylene chloride
  5. customThe methylene chloride phase was separated
  6. extractionextracted with dilute aqueous sodium hydroxide
  7. customThe acidic phase was separated
  8. extractionextracted with methylene chloride
  9. dry with materialThis methylene chloride solution was dried over sodium sulfate
  10. customevaporated
  11. customto remove solvent in vacuo
  12. customto give an oil

Sources & evidence

ORD record
ord-bb1e59601d2c4bf591ab7e8aca869a4a
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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