Hydrogen Bromide → HCID 20217998, compound

HRID 236102Notes

Reaction equation

HRID 236102 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH:10]2[CH2:15][CH2:14][N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C1(O)C=CC=CC=1.[BrH:33]>O>[BrH:33].[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 13607965HCID 13607965, compound

Product 1

HCID 20217998HCID 20217998, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 20.84 g (0.0502 mole) of 4-[(3,4-dichlorophenyl)thio]-1-[(4-methylphenyl)sulfonyl]piperidine, 36.58 g (0.338 mole) of phenol and 200 ml of 48% hydrobromic acid was heated at reflux for 25 hr. The reaction mixture was cooled to room temperature and diluted with water. The aqueous phase was extracted with benzene. The resulting aqueous acidic phase was made alkaline with 10% aqueous sodium hydroxide and extracted with chloroform. The chloroform layer was dried over sodium sulfate, filtered and evaporated to give a residue, the free base of the title compound. The free base was converted to the hydrobromide salt. The salt was recrystallized from methylene chloride-methanol diethyl ether to give 3.6 g (4.4%) of white solid, m.p. 125°-128° C.

Workup

  1. temperatureat reflux for 25 hr
  2. extractionThe aqueous phase was extracted with benzene
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue

Sources & evidence

ORD record
ord-287a82f1c6b24d40a711c7b4ff097627
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

Loading…