Sulfamide → 1-(Propan-2-yl)-1,3-dihydro-2lambda6,1,3-benzothiadiazole-2,2-dione

HRID 1819669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1819669
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])([CH3:3])[CH3:2].[S:12](N)(N)(=[O:14])=[O:13]>N1C=CC=CC=1>[CH:1]([N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH:11][S:12]1(=[O:14])=[O:13])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 82267SulfamideHCID 105587871-N-(propan-2-yl)benzene-1,2-diamine

Produkt 1

HCID 596406791-(Propan-2-yl)-1,3-dihydro-2lambda6,1,3-benzothiadiazole-2,2-dioneAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of N-isopropyl-1,2-phenylenediamine (7.52 g, 50.0 mmol) in pyridine (200 mL) was added sulfamide (7.21 g, 75 mmol, 1.5 equiv.) and the mixture was refluxed for 1 hour. After cooling, pyridine was removed under reduced pressure. Residual pyridine was removed by azeotrope evaporation using toluene. The black residue was dissolved in chloroform (150 mL) and the solution was washed with an aqueous hydrochloric acid solution (2 N, 2×50 mL), water, brine, dried (anhydrous sodium sulfate), and concentrated to give a crude black oil, which was purified by Isco CombiFlash Companion column chromatography (silica gel, 0-40% ethyl acetate/hexane, with 1% formic acid additive) to give 8.61 g (81%) of 1-isopropyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide as a viscous brown liquid.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. custompyridine was removed under reduced pressure
  4. customResidual pyridine was removed by azeotrope evaporation
  5. dissolutionThe black residue was dissolved in chloroform (150 mL)
  6. washthe solution was washed with an aqueous hydrochloric acid solution (2 N, 2×50 mL), water, brine
  7. dry with materialdried (anhydrous sodium sulfate)
  8. concentrationconcentrated
  9. customto give a crude black oil, which
  10. customwas purified by Isco CombiFlash Companion column chromatography (silica gel, 0-40% ethyl acetate/hexane, with 1% formic acid additive)

Quellen und Nachweise

ORD-Eintrag
ord-574a2bb7e1a443ad884b4077ef76c09a
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601744B2

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