Hydrochloric Acid → N-Methyl-N'-methylamino-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochloride

HRID 258745Notes

Reaction equation

HRID 258745 reaction equation
[ClH:1].Cl.O[NH:4][C:5]([NH:17][CH3:18])=[N:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[NH:15][CH:14]=[N:13][C:12]=1[CH3:16].S(O)(O)(=O)=O.[CH3:24][N:25](C(OC(C)(C)C)=O)N.C(=O)([O-])O.[K+].Cl>CN(C)C=O>[ClH:1].[ClH:1].[CH3:18][NH:17][C:5]([NH:4][NH:25][CH3:24])=[N:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[NH:15][CH:14]=[N:13][C:12]=1[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516893Potassium BicarbonateHCID 88794812N-methyl-N-tert-butoxycarbonylhydrazine sulphateHCID 178485010HCID 178485010, compound

Product 1

HCID 178486240N-Methyl-N'-methylamino-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the isothiourea dihydrochloride of Example 1 (i) (6.7 g), N-methyl-N-tert-butoxycarbonylhydrazine sulphate (5.7 g), potassium hydrogen carbonate (10.0 g) and anhydrous dimethylformamide (80 ml) was stirred at 90° C. for 3 hours. After cooling, filtration and concentration to yield the free base, this was heated under reflux with ethanolic hydrogen chloride. Concentration and trituration of the residual product yielded the title compound.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltration and concentration
  3. customto yield the free base
  4. temperaturethis was heated
  5. concentrationConcentration and trituration of the residual product

Sources & evidence

ORD record
ord-ae33860c3be94f0fa9214fab10a9ef6e
Source dataset
uspto-grants-1977_07
Patent number
US04034101

Reaction notes

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