Dimethylformamide → 4-(Pyrrolidin-1-yl)benzene-1-sulfonyl chloride

HRID 641911Notes

Reaction equation

HRID 641911 reaction equation
CN(C=O)C.[N:6]1([C:11]2[CH:16]=[CH:15][C:14]([S:17]([OH:20])(=O)=[O:18])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1.C(Cl)(=O)C([Cl:24])=O>ClCCl>[N:6]1([C:11]2[CH:16]=[CH:15][C:14]([S:17]([Cl:24])(=[O:20])=[O:18])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 221471014-(Pyrrolidin-1-YL)benzenesulfonic acid

Product 1

HCID 534150104-(Pyrrolidin-1-yl)benzene-1-sulfonyl chlorideYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DMF (0.5 mL) was added to solution of 4-(pyrrolidin-1-yl)benzenesulfonic acid (7.3 g, 32.16 mmol) in dichloromethane (40 mL). Oxalyl chloride (10 g, 78.74 mmol) was then dropwise and the resulting solution was maintained at room temperature for 1 hour. The reaction mixture was then quenched by the addition of 40 mL of iced water. The resulting solution was extracted using dichloromethane (3×20 mL), and the organic layers were combined, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system to afford 1.5 g (19%) of 4-(pyrrolidin-1-yl)benzene-1-sulfonyl chloride as a yellow solid. 1H NMR (CDCl3) δ 7.78 (d, 2H), 6.55 (d, 2H), 3.41 (t, 4H), 2.03 (t, 4H).

Workup

  1. customThe reaction mixture was then quenched by the addition of 40 mL of iced water
  2. extractionThe resulting solution was extracted
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3aba208444d5408d908318debc6221c1
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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