Benzenesulfonyl chloride → HCID 23036364, compound

HRID 1709870Notes

Reaction equation

HRID 1709870 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([S:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:30])=[O:29])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 27244364-(Bis(4-fluorophenyl)methylene)piperidine

Product 1

HCID 23036364HCID 23036364, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 15.18 g (0.0529 mole) of 4-[bis(4-flurophenyl)methylene]piperidine and 10,89 g (0.0617 mole) of benzenesulfonyl chloride in 350 ml of pyridine was stirred at room temperature for 16 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sulfuric acid. The methylene chloride solution was extracted with dilute sodium hydroxide, and the methylene chloride solution was dried over sodium sulfate. The solvent was removed in vacuo, and the residue was dissolved in 200 ml of methanol. A precipitate was collected. This was recrystallized from methylene chloride - methanol to give 11.14 g (49.3%) of the title compound as a white solid: mp 180-184° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and dilute sulfuric acid
  3. extractionThe methylene chloride solution was extracted with dilute sodium hydroxide
  4. dry with materialthe methylene chloride solution was dried over sodium sulfate
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue was dissolved in 200 ml of methanol
  7. customA precipitate was collected
  8. customThis was recrystallized from methylene chloride - methanol

Sources & evidence

ORD record
ord-e0d8dcd5dfcc4cb8a4b24f3f6bf7278b
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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