Potassium Bicarbonate → N-Methoxy-N',N"-bis[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine trihydrochloride

HRID 258742Notes

Reaction equation

HRID 258742 reaction equation
[ClH:1].Cl.Cl.O[N:5]([CH2:19][CH2:20][S:21][CH2:22][C:23]1[NH:27][CH:26]=[N:25][C:24]=1[CH3:28])[C:6]([NH2:18])=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17].Cl.[CH3:30][O:31]N.C(=O)([O-])O.[K+]>O>[ClH:1].[ClH:1].[ClH:1].[CH3:30][O:31][NH:18][C:6]([NH:5][CH2:19][CH2:20][S:21][CH2:22][C:23]1[NH:27][CH:26]=[N:25][C:24]=1[CH3:28])=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 178433318HCID 178433318, compound

Product 1

HCID 178502872N-Methoxy-N',N"-bis[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine trihydrochlorideYield 34.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the isothiourea trihydrochloride from Example 2 (ii) (5.1 g), methoxyamine hydrochloride (2.5 g), potassium hydrogen carbonate (5.0 g) and water (30 ml) was refluxed for 24 hours. The products were partitioned between N sodium hydroxide and n-butanol. The n-butanol solution was then extracted with N hydrochloric acid, and the extracts concentrated and dissolved in isopropanol. After filtration from inorganic material, the filtrate gave the title compound (0.6 g). When a solution in aqueous ethanol of this compound was eluted from an ion exchange column of IRA-401 in nitrate form, the corresponding trinitrate was obtained.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customThe products were partitioned between N sodium hydroxide and n-butanol
  3. extractionThe n-butanol solution was then extracted with N hydrochloric acid
  4. concentrationthe extracts concentrated
  5. dissolutiondissolved in isopropanol
  6. filtrationAfter filtration from inorganic material

Sources & evidence

ORD record
ord-0d30c9b3738e4d9e9bad139d165ff8b9
Source dataset
uspto-grants-1977_07
Patent number
US04034101

Reaction notes

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