Sodium Chloride → N-Methoxy-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochloride

HRID 258741

Reaction equation

HRID 258741 reaction equation
[ClH:1].Cl.[OH:3][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].Cl.[CH3:20]ON.C(=O)([O-])O.[K+].[Cl-].[Na+]>O>[ClH:1].[ClH:1].[CH3:20][O:3][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]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 516893Potassium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 178485010HCID 178485010, compound

Product 1

HCID 178485009N-Methoxy-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochlorideYield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the isothiourea dihydrochloride from Example I (i) (6.6 g), methoxyamine hydrochloride (5.0 g), potassium hydrogen carbonate (8.0 g) and water (60 ml) was refluxed for 24 hours. Following cooling, an excess of sodium chloride was added and the solution extracted with chloroform (5×100 ml). The chloroform extracts were concentrated to give the free base which was purified on a column of silica gel by elution with chloroform-methanolic ammonia. After treatment with an excess of ethanolic hydrogen chloride, the residue was triturated with acetonitrile to give the title compound (2.5 g), m.p. 182°-185°.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureFollowing cooling
  3. extractionthe solution extracted with chloroform (5×100 ml)
  4. concentrationThe chloroform extracts were concentrated
  5. customto give the free base which
  6. customwas purified on a column of silica gel by elution with chloroform-methanolic ammonia
  7. customAfter treatment with an excess of ethanolic hydrogen chloride, the residue was triturated with acetonitrile

Sources & evidence

ORD record
ord-86b0d2634dc841e2af52fb5200316428
Source dataset
uspto-grants-1977_07
Patent number
US04034101

Linked notes

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