Phenol → HCID 20218023, compound

HRID 236100Notes

Reaction equation

HRID 236100 reaction equation
C1(O)C=CC=CC=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[S:16][CH:17]1[CH2:22][CH2:21][N:20](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:19][CH2:18]1.[OH-].[Na+]>Br>[ClH:8].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[S:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 13607960HCID 13607960, compound

Product 1

HCID 20218023HCID 20218023, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 200 g (2.13 mole) of phenol, 200 ml of 48% hydrobromic acid and 21.86 g (0.053 mole) of 4-[(2,5-dichlorophenyl)thio]-1-[(4-methylphenyl)sulfonyl]piperidine were heated at reflux for 1.5 hr. The reaction mixture was diluted to 2 liters volume with ice water and made alkaline with 50% sodium hydroxide. The aqueous layer was extracted with diethyl ether. The ether phase was extracted with 1N sulfuric acid. The resulting aqueous acidic phase was extracted with methylene chloride. The methylene chloride phase was dried, filtered and evaporated to remove solvent to give a brown oil, the free base of the title compound. The free base was converted to 9.36 g (59.1%) of a white crystalline hydrochloride salt as in Intermediate 33, m.p. 198°-200° C.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 1.5 hr
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. extractionThe ether phase was extracted with 1N sulfuric acid
  5. extractionThe resulting aqueous acidic phase was extracted with methylene chloride
  6. dry with materialThe methylene chloride phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customto remove solvent
  10. customto give a brown oil

Sources & evidence

ORD record
ord-130ed77f5ce8490792b92bec26295b8b
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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