Chlorosulfonic acid → 3-(Pyrrolidin-1-YL)benzene-1-sulfonyl chloride

HRID 641913Notes

Reaction equation

HRID 641913 reaction equation
[C:1]1([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:12]([Cl:16])(=O)(=[O:14])[OH:13]>>[N:7]1([C:1]2[CH:6]=[C:5]([S:12]([Cl:16])(=[O:14])=[O:13])[CH:4]=[CH:3][CH:2]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 777261-Phenylpyrrolidine

Product 1

HCID 534147063-(Pyrrolidin-1-YL)benzene-1-sulfonyl chlorideYield 7%

Conditions

Temperature
60 °C

Procedure

1-phenylpyrrolidine (4.3 g, 29.25 mmol) was added dropwise to sulfurochloridic acid (20 mL) at 0° C. and the resulting solution was then maintained at 60° C. overnight. The reaction mixture was then quenched by adding 200 mL of ice/salt. The resulting solution was extracted with ethyl acetate (3×100 mL), and the organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography using a 1:500 ethyl acetate/petroleum ether solvent system. The collected fractions were combined and concentrated to give 0.5 g (7%) of 3-(pyrrolidin-1-yl)benzene-1-sulfonyl chloride as a yellow solid. 1H NMR (CDCl3) δ 7.36 (m, 1H), 7.24 (d, 1H), 7.07 (s, 1H), 6.82 (d, 1H), 3.34 (t, 4H), 2.05 (t, 4H).

Workup

  1. customThe reaction mixture was then quenched
  2. additionby adding 200 mL of ice/salt
  3. extractionThe resulting solution was extracted with ethyl acetate (3×100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2f6a3122cebc4e03b2e1cbd558c92a43
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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