Sodium Methoxide → HCID 22416545, compound

HRID 1720927Notes

Reaction equation

HRID 1720927 reaction equation
Cl.[O:2]([CH2:6][CH2:7][NH2:8])[N+:3]([O-:5])=[O:4].C[O-].[Na+].[C:12]([N:14]=[C:15]([C:20]1[CH:21]=[N:22][C:23]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:24][CH:25]=1)OCCC)#[N:13]>CO>[C:12]([NH:14][C:15]([C:20]1[CH:21]=[N:22][C:23]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:24][CH:25]=1)=[N:8][CH2:7][CH2:6][O:2][N+:3]([O-:5])=[O:4])#[N:13]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 18358043HCID 18358043, compoundHCID 22416571HCID 22416571, compound

Product 1

HCID 22416545HCID 22416545, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-nitroxyethylamine hydrochloride (314 mg, 2.20 mmol) in methanol (3 ml) was added sodium methoxide (115 mg, 2.13 mmol) followed by a solution of propyl N-cyano-6-diethylamino-3-pyridinecarboximidate (370 mg, 1.42 mmol) in methanol (2 ml), and the mixture was stirred at room temperature for 5 hours. After the reaction was completed, the reaction mixture was concentrated to dryness under reduced pressure. The residue was suspended in water and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography with a mixed solvent of ethyl acetate and hexane as an eluent to give the title compound (183 mg, yield 42%) as colorless crystals.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography with a mixed solvent of ethyl acetate and hexane as an eluent

Sources & evidence

ORD record
ord-907b99e3ed78467c87211a267cd4ba70
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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