Hydrochloric Acid → HCID 18334147, compound

HRID 2269420Notes

Reaction equation

HRID 2269420 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:19]=[N+]=[N-])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[ClH:42]>O1CCCC1.C(OCC)(=O)C>[ClH:42].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH2:19])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 18334250HCID 18334250, compound

Product 1

HCID 18334147HCID 18334147, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triphenylphosphinie (20.5 g) was added in small portions to a solution of α-(4-methoxyphenyl)-3-nitrobenzyl azide (18.5 g) [prepared as described in step (a) above] in anhydrous tetrahydrofuran (100 ml). When the triphenylphosphine was dissolved and the evolution of nitrogen had ceased, water (20 ml) was added to the reaction mixture and this mixture was heated under reflux for 6 hours. At the end of this time, the tetrahydrofuran of the reaction mixture was removed by evaporation under reduced pressure. The residue was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column using a 2:1 by volume mixture of hexane and ethyl acetate as the eluant, to afford a colorless oil. This oil was dissolved in a solution of hydrogen chloride in ethyl acetate (4N). The ethyl acetate was evaporated to dryness. The residue was suspended in diisopropyl ether and filtered to afford the title compound (13.8 g) as a white solid.

Workup

  1. temperaturethis mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customAt the end of this time, the tetrahydrofuran of the reaction mixture was removed by evaporation under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residue was purified by chromatography through a silica gel column
  9. additionby volume mixture of hexane and ethyl acetate as the eluant
  10. customto afford a colorless oil
  11. customThe ethyl acetate was evaporated to dryness
  12. filtrationfiltered

Sources & evidence

ORD record
ord-3670fd8966464a7aa2be3e6dd6e6bb15
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…