Hydrochloric Acid → Pyridyldithioethylamine

HRID 2403500Notes

Reaction equation

HRID 2403500 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 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).

Workup

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

Sources & evidence

ORD record
ord-db561d5b85c749c680075cb2a37f026b
Source dataset
uspto-grants-2014_08
Patent number
US08802667B2

Reaction notes

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