1,3-Benzodioxole → 1,3-Benzodioxole-5-sulfonyl chloride

HRID 8843

Reaction equation

HRID 8843 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7]1>CN(C)C=O>[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:14][C:9]=2[O:8][CH2:7]1

Participants

4

Reactant 2

HCID 92291,3-BenzodioxoleHCID 24648Sulfuryl chloride

Product 1

HCID 49134011,3-Benzodioxole-5-sulfonyl chlorideYield 16.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4.25 g of anhydrous N,N-dimethylformamide at 0° C. under nitrogen was added 7.84 g of sulfuryl chloride, whereupon a solid formed. After stirring for 15 minutes, 6.45 g of 1,3-benzodioxole was added, and the mixture heated at 100° C. for 2 hours. The reaction was cooled, poured into ice water, extracted with methylene chloride, dried over magnesium sulfate, filtered and concentrated to give 7.32 g of crude material as a black oil. This was chromatographed on silica gel using 20% methylene chloride/hexane to afford 1.9 g of (1,3-benzodioxol-5-yl)sulfonyl chloride.

Workup

  1. customwhereupon a solid formed
  2. temperatureThe reaction was cooled
  3. extractionextracted with methylene chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 7.32 g of crude material as a black oil
  8. customThis was chromatographed on silica gel using 20% methylene chloride/hexane

Sources & evidence

ORD record
ord-771a37b166694f87a54ba1bf13c55b3c
Source dataset
uspto-grants-2006_08
Patent number
US07091219B2

Linked notes

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