Sodium Methoxide → 3-[(4-Methoxyphenyl)sulfonyl]pyrrolidine hydrochloride

HRID 236089Notes

Reaction equation

HRID 236089 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:17][O-:18].[Na+]>CS(C)=O>[ClH:2].[CH3:17][O:18][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 202178543-((4-Chlorophenyl)sulfonyl)pyrrolidine hydrochloride

Product 1

HCID 202178603-[(4-Methoxyphenyl)sulfonyl]pyrrolidine hydrochloride

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 15.5 g (0.060 mole) of 3-[(4-chlorophenyl)sulfonyl]pyrrolidine hydrochloride and 9.0 g (0.167 mole) of sodium methoxide in 200 ml of dimethylsulfoxide was stirred at 100° C. for 2 hours. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and water. The methylene chloride solution was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil, the free base of the title compound. The hydrochloride salt was prepared, recrystallizing from methanol-diethyl ether to give 9.1 g (55%) of white crystalline solid, m.p. 181°-182° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and water
  3. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto give an oil

Sources & evidence

ORD record
ord-86d6f2488d54497e85f9236dc76824c2
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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