4-Methoxybenzenesulfonyl chloride → HCID 247207, compound

HRID 1020461Notes

Reaction equation

HRID 1020461 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 247207HCID 247207, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

4-Methoxy-benzenesulfonyl chloride (3.00 g, 14.52 mmol) was slowly added to a solution of pyrrolidine (5.15 g, 72.6 mmol) in CHCl3 (15 mL) with stirring at 0° C. The reaction mixture was allowed to warm up to room temperature and then stirred for 1 hour. After that the reaction mixture was concentrated in vacuo. The residue was dissolved in toluene and washed with aqueous H3PO4 solution, and then aqueous KHCO3 solution. The organic phase was dried with Na2SO4, and filtered. The solvents were removed in vacuo and the residue crystallized from ether and heptane to provide the title compound (3.21 g, m.p. 88-89° C.).

Workup

  1. temperatureto warm up to room temperature
  2. stirringstirred for 1 hour
  3. concentrationAfter that the reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in toluene
  5. washwashed with aqueous H3PO4 solution
  6. dry with materialThe organic phase was dried with Na2SO4
  7. filtrationfiltered
  8. customThe solvents were removed in vacuo
  9. customthe residue crystallized from ether and heptane

Sources & evidence

ORD record
ord-7f0c53a315684873bed54c2a82112cb4
Source dataset
uspto-grants-2014_05
Patent number
US08716345B2

Reaction notes

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