Cyanamide → HCID 22416544, compound

HRID 1720903Notes

Reaction equation

HRID 1720903 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:9](=[NH:14])[O:10][CH2:11][CH2:12][CH3:13])[CH:6]=[N:7][CH:8]=1)[CH3:2].[N:15]#[C:16]N>C(#N)C>[C:16]([N:14]=[C:9]([C:5]1[CH:6]=[N:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=1)[O:10][CH2:11][CH2:12][CH3:13])#[N:15]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 22416569Propyl 5-ethyl-3-pyridinecarboximidate

Product 1

HCID 22416544HCID 22416544, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The propyl 5-ethyl-3-pyridinecarboximidate were then dissolved in acetonitrile (5 ml), and an aqueous solution (30 ml) of cyanamide (1.13 g, 26.9 mmol), Na2HPO4 (1.29 g, 9.1 mmol) and NaH2PO4 ·2H2O (8.45 g, 54.2 mmol) was added to the solution. The mixture was stirred at room temperature for 19 hours. After reaction, the mixture was extracted with chloroform (50 ml×2). The chloroform layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and subjected to silica gel column chromatography (Wako Gel C-200, 50 g; eluted with hexane:ethyl acetate=5:1) to give 1.51 g (7.0 mmol) of propyl N-cyano-5-ethyl-3-pyridinecarboximidate (yield, 44%).

Workup

  1. customAfter reaction
  2. extractionthe mixture was extracted with chloroform (50 ml×2)
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washsubjected to silica gel column chromatography (Wako Gel C-200, 50 g; eluted with hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-cf33ff407d18468cbd17cba88a3d1a5d
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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