Thiophenol → HCID 13607955, compound

HRID 236085Notes

Reaction equation

HRID 236085 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].Cl[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:15]1>CN(C)C=O>[CH3:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([N:16]2[CH2:17][CH2:18][CH2:19][CH:14]([CH2:13][S:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:15]2)(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 13607973HCID 13607973, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13607955HCID 13607955, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.0808 mole of sodium hydride in 250 ml of dry dimethylformamide at room temperature and under nitrogen atmosphere was added 9.0 g (0.0818 mole) of thiophenol. After evolution of hydrogen had stopped, 14.18 g (0.0494 mole) of 3-chloromethyl-1-[(4-methylphenyl)sulfonyl]piperidine was added and the solution was stirred at 100°-110° C. for 17 hr. The solution was quenched in 500 ml of 1M sodium hydroxide and the aqueous mixture was extracted with several portions of methylene chloride. The methylene chloride solution was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil which solidified on standing. Recrystallization from methylene chloride-diethyl ether-hexane gave 14.65 g (82%) of the product, m.p. 66.67° C.

Workup

  1. customThe solution was quenched in 500 ml of 1M sodium hydroxide
  2. extractionthe aqueous mixture was extracted with several portions of methylene chloride
  3. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto give an oil which
  6. customRecrystallization from methylene chloride-diethyl ether-hexane

Sources & evidence

ORD record
ord-6b41469cce3645a496980729383ef87c
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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