Sodium Azide → HCID 57437974, compound

HRID 227575Notes

Reaction equation

HRID 227575 reaction equation
[CH3:1][C:2]1[C:3](=O)[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][NH:6][CH:7]=1.[N-:14]=[N+:15]=[N-:16].[Na+]>P(Cl)(Cl)(Cl)=O>[N:14]([C:3]1[C:2]([CH3:1])=[CH:7][N:6]=[CH:5][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N+:15]=[N-:16]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 82465572676-90-5

Product 1

HCID 57437974HCID 57437974, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
95 °C

Procedure

A slurry of 14.1 g (78 mmol) of ethyl 1,4-dihydro-5-methyl-4oxo-3-pyridinecarboxylate (prepared according to Horvath, G.; Dvortsak, P. J. Heterocycl. Chem. 1980, 359) in 30 mL of phosphorous oxychloride was refluxed for 1 hour. After cooling, the volatiles were removed with a rotary evaporator. The residue was poured into cold saturated aqueous sodium bicarbonate. Dichloromethane was added and the mixture was filtered through celite. The layers were separated. The organic layer was dried (sodium sulfate) and the solvent was removed with a rotary evaporator. The residue was dissolved in 150 mL of dimethylformamide. 15.2 g (234 mmol) of sodium azide was added. The mixture was heated at 95° C. for 1 hour. After cooling, the solvent was removed with a rotary evaporator. The residue was partitioned between ethyl acetate and water. The organic layer was dried (sodium sulfate) and the solvent was removed with a rotary evaporator. The residue was passed through a plug of silica gel with 25% ethyl acetate in hexanes as eluant to afford 11.9 g of the title compound as a cream colored solid.

Workup

  1. temperatureAfter cooling
  2. customthe volatiles were removed with a rotary evaporator
  3. additionThe residue was poured into cold saturated aqueous sodium bicarbonate
  4. additionDichloromethane was added
  5. filtrationthe mixture was filtered through celite
  6. customThe layers were separated
  7. dry with materialThe organic layer was dried (sodium sulfate)
  8. customthe solvent was removed with a rotary evaporator
  9. dissolutionThe residue was dissolved in 150 mL of dimethylformamide
  10. temperatureAfter cooling
  11. customthe solvent was removed with a rotary evaporator
  12. customThe residue was partitioned between ethyl acetate and water
  13. dry with materialThe organic layer was dried (sodium sulfate)
  14. customthe solvent was removed with a rotary evaporator

Sources & evidence

ORD record
ord-a04c5d9f50c34bf9b1351961ade63a4b
Source dataset
uspto-grants-2009_07
Patent number
US07560564B2

Reaction notes

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