Hydrochloric Acid → Pyridyldithioethylamine

HRID 2405716

Reaktionsgleichung

Reaktionsgleichung von HRID 2405716
[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-f4ff4f28f1ba43c2a8ba4a3ce201bd4a
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809320B2

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