p-Chlorothiophenol → HCID 13607969, compound

HRID 1981782Notes

Reaction equation

HRID 1981782 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]1[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]2[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 14798Sodium HydroxideHCID 20217776HCID 20217776, compound

Product 1

HCID 13607969HCID 13607969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 280 g (1.94 mole) of p-chlorothiophenol and 120 ml of 50% sodium hydroxide in 1 liter of dimethylformamide was stirred for 15 min at 25° C. One mole of 2-chloromethyl-1-(phenylsulfonyl)piperidine was added and the solution was stirred at 60° C. for 65 hr. The mixture was quenched in water and the aqueous mixture was extracted with methylene chloride. The methylene chloride solution was extracted with several portions of dilute sodium hydroxide and evaporated in vacuo to give an oil. The oil was crystallized from methanol to give solid product, m.p. 78.5°-80° C.

Workup

  1. stirringthe solution was stirred at 60° C. for 65 hr
  2. customThe mixture was quenched in water
  3. extractionthe aqueous mixture was extracted with methylene chloride
  4. extractionThe methylene chloride solution was extracted with several portions of dilute sodium hydroxide
  5. customevaporated in vacuo
  6. customto give an oil
  7. customThe oil was crystallized from methanol
  8. customto give solid product, m.p. 78.5°-80° C.

Sources & evidence

ORD record
ord-5a536a531f834c6c9ea1cfc739159e0d
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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