2-(3-Chloropyrid-2-ylmethylthio)ethylamine → N-Methyl-N'-[2-(3-chloropyrid-2-ylmethylthio)ethyl]-amidinosulphonic acid

HRID 354533Notes

Reaction equation

HRID 354533 reaction equation
[Cl:1][C:2]1[C:3]([CH2:8][S:9][CH2:10][CH2:11][NH2:12])=[N:4][CH:5]=[CH:6][CH:7]=1.CS[C:15](=[N:20][CH3:21])[S:16]([O-:19])(=[O:18])=[O:17]>C(#N)C.CO>[CH3:21][NH:20][C:15]([S:16]([OH:19])(=[O:18])=[O:17])=[N:12][CH2:11][CH2:10][S:9][CH2:8][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 129515322-(3-Chloropyrid-2-ylmethylthio)ethylamineHCID 867370781-Methylthio-1-methyliminomethanesulphonate

Product 1

HCID 178484988N-Methyl-N'-[2-(3-chloropyrid-2-ylmethylthio)ethyl]-amidinosulphonic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-(3-chloropyrid-2-ylmethylthio)ethylamine (2.03 g) in dry acetonitrile (150 ml) was added dropwise, with stirring, to a solution of 1-methylthio-1-methyliminomethanesulphonate (1.69 g) in dry acetonitrile (150 ml) at 50°. The mixture was stirred at 60° for 30 minutes and then allowed to cool. The mixture was stripped to dryness, dissolved in methanol and absorbed onto silica gel. Chromatography on a column of silica gel produced a viscous oil which was collected by eluting the column with a chloroform/methanol mixture and evaporating off the solvent. The viscous oil analysed by micro-analysis and nuclear magnetic resonance spectroscopy to the title compound.

Workup

  1. temperatureto cool
  2. customabsorbed onto silica gel
  3. customChromatography on a column of silica gel produced a viscous oil which
  4. customwas collected
  5. washby eluting the column with a chloroform/methanol mixture
  6. customevaporating off the solvent

Sources & evidence

ORD record
ord-cf2704a20e104db0aa42ef7a1c39e163
Source dataset
uspto-grants-1983_03
Patent number
US04375472

Reaction notes

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