Hydrochloric Acid → Pyridyldithioethylamine

HRID 1776676

Reaktionsgleichung

Reaktionsgleichung von HRID 1776676
[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-d3f877cfe87e4ce59561616f83da9153
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265841B2

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