N-Benzylethylenediamine → 2-Benzyl-1,2,5-thiadiazolidine 1,1-dioxide

HRID 560550

Reaktionsgleichung

Reaktionsgleichung von HRID 560550
[CH2:1]([NH:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:12](N)(N)(=[O:14])=[O:13]>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][NH:11][S:12]1(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 77801N-BenzylethylenediamineHCID 82267Sulfamide

Produkt 1

HCID 103758902-Benzyl-1,2,5-thiadiazolidine 1,1-dioxideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of N-benzylethane-1,2-diamine (1.00 g, 6.65 mmol) in pyridine (10 mL) was added sulfamide (0.77 g, 7.98 mmol). The mixture was refluxed for 16 hours. The solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), washed with water (200 mL) and brine (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate/hexane (1/4) to afford the title compound as an oily solid in 40% yield (0.57 g): 1H NMR (300 MHz, CDCl3) δ 7.35-7.27 (m, 5H), 4.59 (br s, 1H), 4.15 (s, 2H), 3.48-3.42 (m, 2H), 3.27-3.22 (m, 2H); MS (ES+) m/z 213.2 (M+1).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 16 hours
  2. customThe solvent was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate (100 mL)
  4. washwashed with water (200 mL) and brine (100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluted with ethyl acetate/hexane (1/4)

Quellen und Nachweise

ORD-Eintrag
ord-e14c6f0b0c3943e1a443ce0b6e6e5565
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063084B2

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