Hydrochloric Acid → Pyridyldithioethylamine

HRID 2403500

Reaktionsgleichung

Reaktionsgleichung von HRID 2403500
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][NH:11]C(=O)OC(C)(C)C.Cl>C(O)C.C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][NH2:11]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 21028185Tert-butyl (2-(pyridin-2-yldisulfanyl)ethyl)carbamate

Produkt 1

HCID 128546PyridyldithioethylamineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

tert-Butyl 2-(pyridin-2-yldisulfanyl)ethylcarbamate (1.06 g, 3.70 mmol) in 16 ml of EtAc was added 4.0 ml of HCl (conc.) at RT. The mixture was stirred at RT for 0.5 h, diluted with ethanol/toluene (6 ml, 1:1), evaporated and co-evaporated with ethanol/toluene (3×10 ml), crystallized with ethanol/EtAc/Hexane, filtered, and dried over a vacuum to afford 135 mg (88%) of the title compound. 1H NMR (CD3OD) 7.58 (m, 1H), 7.47 (m, 1H), 7.06 (m, 1H), 6.83 (m, 1H), 3.34 (m, 2H), 3.02 (m, 2H); 13C NMR 158.69, 149.07, 137.81, 122.48, 120.98, 39.52, 36.94; MS m/z+187.10 (M+H).

Aufarbeitung

  1. customevaporated
  2. customcrystallized with ethanol/EtAc/Hexane
  3. filtrationfiltered
  4. customdried over a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-db561d5b85c749c680075cb2a37f026b
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802667B2

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