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

HRID 258741

Reaktionsgleichung

Reaktionsgleichung von HRID 258741
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 178485009N-Methoxy-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochlorideAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-86b0d2634dc841e2af52fb5200316428
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04034101

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