Ethanol, 2-amino-, 1-nitrate, nitrate (1:1) → N-cyano-N'-(2-nitroxyethyl)-4-pyridinecarboximidamide
Reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)OC(C)C)#[N:2].[N+]([O-])(O)=O.[O:19]([CH2:23][CH2:24][NH2:25])[N+:20]([O-:22])=[O:21].C[O-].[Na+]>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)=[N:25][CH2:24][CH2:23][O:19][N+:20]([O-:22])=[O:21])#[N:2]Participants
5
Procedure
Isopropyl N-cyano-4-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (10 ml), and 2-nitroxyethylamine nitrate (0.57 g, 2.9 mmol) and sodium methoxide (0.18 g, 2.9 mmol) were added. The mixture was stirred at room temperature for 10 minutes. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residue thus obtained was extracted with dichloromethane (50 ml×3). The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual concentrate was crystallized from dichloromethane-diethyl ether to give the title compound (0.37 g, 1.6 mmol, yield: 61%) as colorless needles.
Workup
- concentrationthe reaction solution was concentrated under reduced pressure
- customThe residue thus obtained
- extractionwas extracted with dichloromethane (50 ml×3)
- dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- concentrationThe residual concentrate
- customwas crystallized from dichloromethane-diethyl ether
Sources & evidence
- ORD record
- ord-036329a149b24b42988b4bd457b4a159
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05223508
Reaction notes
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