Hydrochloric Acid → Pyridyldithioethylamine

HRID 1968493

Reaction equation

HRID 1968493 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 128546PyridyldithioethylamineYield 88%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

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 vaccum 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).

Workup

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

Sources & evidence

ORD record
ord-9a02e2f4e7ce41e0a6e430e1b2e16054
Source dataset
uspto-grants-2013_04
Patent number
US08426402B2

Linked notes

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