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3-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester → N-cyano-N'-(4-ethyl-2,4-hexadien-1-yl)-3-pyridinecarboximidamide

HRID 2295004
Notes
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Reaction equation

HRID 2295004 reaction equation
[CH2:1]([C:3](=[CH:8][CH3:9])[CH:4]=[CH:5][CH2:6][NH2:7])[CH3:2].[C:10]([N:12]=[C:13]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)OC(C)C)#[N:11].C[O-].[Na+]>CO.O>[C:10]([NH:12][C:13]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[N:7][CH2:6][CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH3:9])#[N:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl esterHCID 10942334Sodium MethoxideHCID 539452134-Ethyl-2,4-hexadien-1-ylamine

Product 1

HCID 54082574N-cyano-N'-(4-ethyl-2,4-hexadien-1-yl)-3-pyridinecarboximidamideYield 80.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×
HCID 962WaterSolvent

Procedure

To a solution of crude 4-ethyl-2,4-hexadien-1-ylamine (1.38 g) and isopropyl N-cyano-3-pyridinecarboximidate (1.74 g) in methanol (35 ml) at room temperature was added 28% sodium methoxide in methanol (2.13 g). After 10 minutes, the mixture was diluted with water and extracted three times with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (5% methanol in dichloromethane) to give N-cyano-N'-(4-ethyl-2,4-hexadien-1-yl)-3-pyridinecarboximidamide (1.89 g) as an oil.

Workup

  1. extractionextracted three times with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8ab4389acb59469e8bb672d3a15c4a6a
Source dataset
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05691366

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes