Ammonia → 3-(1,3-Dioxolan-2-yl)thiophene-2-sulfonamide

HRID 580426Notes

Reaction equation

HRID 580426 reaction equation
[NH3:1].[O:2]1[CH2:6][CH2:5][O:4][CH:3]1[C:7]1[CH:11]=[CH:10][S:9][C:8]=1[S:12](Cl)(=[O:14])=[O:13]>O1CCCC1>[O:2]1[CH2:6][CH2:5][O:4][CH:3]1[C:7]1[CH:11]=[CH:10][S:9][C:8]=1[S:12]([NH2:1])(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 105389153-(1,3-dioxolan-2-yl)thiophene-2-sulfonyl Chloride

Product 1

HCID 138817523-(1,3-Dioxolan-2-yl)thiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5 ml of liquified ammonia gas dissolved in 50 ml of tetrahydrofuran was added dropwise with stirring and cooling 12.7 g of 3-(1,3-dioxolan-2-yl)thiophene-2-sulfonyl chloride. After stirring overnight at ambient temperature, the tetrahydrofuran was removed in vacuo, water was added to the residue and the mixture was extracted twice with 75 ml of methylene chloride. After washing the combined methylene chloride extracts with water, drying over magnesium sulfate, filtering off the drying agent and evaporation of the methylene chloride, an oily solid residue was obtained. This was chromatographed through silica gel using 1:1 ethyl acetate-hexanes as eluant (Rf 0.35). Evaporation of the solvent mixture yielded 2.2 g of the desired product, as a waxy solid. Infrared absorption spectra showed peaks at 3360, 3260, 1340 and 1140 cm-1, consistent for a primary sulfonamide. Mass spectrum analysis: calc. 235, found 234 (Mass-1H).

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring overnight at ambient temperature
  3. customthe tetrahydrofuran was removed in vacuo, water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted twice with 75 ml of methylene chloride
  6. washAfter washing the combined methylene chloride
  7. dry with materialdrying over magnesium sulfate
  8. filtrationfiltering off
  9. customthe drying agent and evaporation of the methylene chloride
  10. customan oily solid residue was obtained
  11. customThis was chromatographed through silica gel using 1:1 ethyl acetate-hexanes as eluant (Rf 0.35)
  12. customEvaporation of the solvent mixture

Sources & evidence

ORD record
ord-35fb095804994ea6acd20e43edf73dc9
Source dataset
uspto-grants-1988_06
Patent number
US04753672

Reaction notes

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