Sodium Hydroxide → HCID 12826447, compound

HRID 903619Notes

Reaction equation

HRID 903619 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[N:12][C:13]3[C:20]4([CH3:23])[CH2:21][CH2:22][CH:17]([C:18]([CH3:25])([CH3:24])[O:19]4)[C:14]=3[N+:15]=2[O-])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)Cl.[OH-].[Na+]>ClCCCl>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[N:12][C:13]3[C:20]4([CH3:23])[CH2:21][CH2:22][CH:17]([C:18]([CH3:25])([CH3:24])[O:19]4)[C:14]=3[N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24387Phosphorus trichlorideHCID 23337019HCID 23337019, compound

Product 1

HCID 12826447HCID 12826447, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a flask equipped with stirrer, reflux condenser and gas inlet there is added under nitrogen a mixture of 6.9 g. (0.020 mole) of (+)-3-(m-nitrophenyl)-5,8-dihydro-6,6,8-trimethyl-5,8-ethano-6H-pyrano[4,3-e]-as-triazine-4-oxide, 20 ml. (0.23 mole) of phosphorous trichloride in 300 ml. of 1,2-dichloroethane. The resulting mixture is refluxed for 6.5 hours and then cooled to room temperature, and poured into a beaker containing 500 g. of ice. To this mixture there is added cautiously 60 ml. of 50% aqueous sodium hydroxide while maintaining stirring for 1 hour. The resulting mixture is then transferred to a separatory funnel and permitted to separate. The layers are partitioned and the aqueous phase extracted twice with 300 ml. of methylene chloride and the extracts combined with the organic phase. The resulting solution is washed once with brine, dried over anhydrous magnesium sulfate, and then concentrated to yield a residue which is then recrystallized from absolute ethanol to give (-)-3-(m-nitrophenyl)-5,8-dihydro-6,6,8-trimethyl-5,8-ethano-6H-pyrano[4,3-e]-as-triazine; m.p. 184° to 185° C.; ORD-1.8°.

Workup

  1. customTo a flask equipped with stirrer
  2. temperaturereflux condenser and gas inlet
  3. additionthere is added under nitrogen
  4. additiona mixture of 6.9 g
  5. temperatureThe resulting mixture is refluxed for 6.5 hours
  6. additionpoured into a beaker
  7. additioncontaining 500 g
  8. additionTo this mixture there is added cautiously 60 ml
  9. customThe resulting mixture is then transferred to a separatory funnel
  10. customto separate
  11. customThe layers are partitioned
  12. extractionthe aqueous phase extracted twice with 300 ml
  13. washThe resulting solution is washed once with brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated
  16. customto yield a residue which
  17. customis then recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-33f46e96b1d54ec1abd880f68cb0eabe
Source dataset
uspto-grants-1980_10
Patent number
US04228280

Reaction notes

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