Triethylamine → N-cyano-N'-(2-nitroxyethyl)pyrazinecarboximidamide

HRID 374186

Reaction equation

HRID 374186 reaction equation
[C:1]([N:3]=[C:4]([C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1)OC)#[N:2].[N+]([O-])(O)=O.[O:17]([CH2:21][CH2:22][NH2:23])[N+:18]([O-:20])=[O:19].C(N(CC)CC)C>CO>[C:1]([NH:3][C:4]([C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1)=[N:23][CH2:22][CH2:21][O:17][N+:18]([O-:20])=[O:19])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 10057818Methyl N-cyanopyrazinecarboximidate

Product 1

HCID 10331652N-cyano-N'-(2-nitroxyethyl)pyrazinecarboximidamideYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl N-cyanopyrazinecarboximidate (0.49 g, 3.0 mmol) was dissolved in methanol (6 ml), 2-nitroxyethylamine nitrate (1.01 g, 6.0 mmol) and triethylamine (1.01 g, 10.0 mmol) were added. The mixture was stirred at room temperature for 46 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residue thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C 200, 30 g) eluting with chloroform-methanol (300:1). The eluted fractions were concentrated under reduced pressure and crystallized from diethyl ether to give the title compound (0.18 g, 0.78 mmol, yield: 26%) as colorless crystals.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. washeluting with chloroform-methanol (300:1)
  4. concentrationThe eluted fractions were concentrated under reduced pressure
  5. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-c8529e887c1041cf90a5fa40260146ca
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Linked notes

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