Water → 1-(4-(Naphthalen-2-ylsulfonyl)piperazin-1-yl)-2-(p-tolylthio)ethanone

HRID 516988Notes

Reaction equation

HRID 516988 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([S:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:11].[C:31](=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[S:18]([N:15]1[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][S:7][C:1]2[CH:6]=[CH:5][C:4]([CH3:31])=[CH:3][CH:2]=2)[CH2:13][CH2:14]1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 24058752-Chloro-1-[4-(naphthalene-2-sulfonyl)piperazin-1-yl]ethan-1-one2×

Product 1

HCID 679804581-(4-(Naphthalen-2-ylsulfonyl)piperazin-1-yl)-2-(p-tolylthio)ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Thio phenol (100 mg, 0.85 mmol), 2-chloro-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone (compound 5, 0.3 g, 0.85 mmol) and anhydrous potassium carbonate (0.293 g, 2.125 mmol) were stirred for over night in dry acetonitrile (20 mL). The mixture was then stirred into a large volume of water and the solution extracted with ether. Unreacted phenol was removed with cold 1N NaOH solution. The ether extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to yield the title compound in quantitative yield.

Workup

  1. extractionthe solution extracted with ether
  2. customwas removed with cold 1N NaOH solution
  3. extractionThe ether extract
  4. dry with materialwas dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-85b568c8e02a40d98e558e478bd289fe
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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