Hydrochloric Acid → S-3-(Methylamino)propyl ethanethioate hydrogen chloride salt

HRID 2405715Notes

Reaction equation

HRID 2405715 reaction equation
[C:1](=[O:16])([S:3][CH2:4][CH2:5][CH2:6][N:7](C(OC(C)(C)C)=O)[CH3:8])[CH3:2].[ClH:17]>C(O)C.C1(C)C=CC=CC=1>[ClH:17].[C:1](=[O:16])([S:3][CH2:4][CH2:5][CH2:6][NH:7][CH3:8])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14194552S-3-(tert-butoxycarbonyl(methyl)amino)propyl ethanethioate

Product 1

HCID 86644083S-3-(Methylamino)propyl ethanethioate hydrogen chloride saltYield 88%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

S-3-(tert-Butoxycarbonyl(methyl)amino)propyl ethanethioate (206 mg, 0.834 mmol) in 4 ml of EtAc was added 1.0 ml of HCl (conc.) at RT. The mixture was stirred at RT for 1 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 (CDCl3) 9.70 (br, 1H), 8.56 (br, 1H), 3.42 (m, 2H), 2.52 (m, 2H), 2.35 (s, 3H), 2.05 (s, 3H), 1.88 (m, 2H); 13C NMR 174.64, 40.57, 31.57, 27.69, 20.94, 15.62; MS m/z+ 170.0 (M+Na), 148.10 (M+H).

Workup

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

Sources & evidence

ORD record
ord-d3dd4ce8afa24ebdbd40b25dc4b29a0c
Source dataset
uspto-grants-2014_08
Patent number
US08809320B2

Reaction notes

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