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

HRID 354534Notes

Reaction equation

HRID 354534 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>[Cl:1][C:2]1[C:3]([CH2:8][S:9][CH2:10][CH2:11][NH:12][C:15]([S:16]([OH:19])(=[O:17])=[O:18])=[N:20][CH2:21][CH2:10][S:9][CH2:8][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 53709668N,N'-bis-[2-(3-chloropyrid-2-ylmethylthio)ethyl]amidinosulphonic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-(3-chloropyrid-2 ylmethylthio)ethylamine (4.06 g) in dry acetonitrile (200 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 stired at 60° for 1 hour and then allowed to cool. The mixture was evaporated 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 microanalysis and nuclear magnetic resonance spectroscopy to the title compound.

Workup

  1. temperatureto cool
  2. customThe mixture was evaporated to dryness
  3. dissolutiondissolved in methanol
  4. customabsorbed onto silica gel
  5. customChromatography on a column of silica gel produced a viscous oil which
  6. customwas collected
  7. washby eluting the column with a chloroform/methanol mixture
  8. customevaporating off the solvent

Sources & evidence

ORD record
ord-7a170a13c2544bd194e9399aa7524e56
Source dataset
uspto-grants-1983_03
Patent number
US04375472

Reaction notes

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