Hydrochloric Acid → HCID 14745571, compound

HRID 543078Notes

Reaction equation

HRID 543078 reaction equation
C1(N=[N:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Te:15](Cl)(Cl)Cl)C=CC=CC=1.[BH4-].[Na+].[C:21](OC(=O)CC)(=O)[CH2:22][CH3:23].Cl>C(O)C>[CH2:22]([C:23]1[Te:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=1)[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31263Propionic anhydrideHCID 4311764Sodium borohydrideHCID 13931220HCID 13931220, compound

Product 1

HCID 14745571HCID 14745571, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Phenylazophenyltellurium trichloride (Preparation A) (10.4 g, 0.025 mole) was suspended in ethanol (100 ml) in a flask equipped with a nitrogen gas inlet, magnetic stirrer, reflux condenser, and powder addition funnel. While stirring, under a nitrogen atmosphere, at room temperature, sodium borohydride (3.8 g, 0.10 mole) was added in increments at a rate sufficient to maintain a vigorous exothermic reaction. Stirring of the reaction mixture at room temperature was continued for 30 minutes after the addition was complete, maintaining the nitrogen atmosphere. A thermometer was inserted while still maintaining a nitrogen atmosphere and propionic anhydride (3.9 g, 0.03 mole) was added dropwise. The reaction temperature rose from 25° C. to 30° C. Upon completion of the addition, stirring was continued until the temperature returned to 25° C. Concentrated hydrochloric acid (25 ml) was added dropwise to the reaction mixture, resulting in formation of a black solid. The temperature rose to around 50° C. Stirring was continued until the temperature returned to 25° C. The black solid was removed by filtration, and washed with ethanol, and discarded. The filtrate was concentrated in a rotary evaporator, diluted with about an equal volume of water, filtered through a Celite® pad, and neutralized to a pH of about 7 with sodium bicarbonate. Extraction with diethyl ether and removal of the ether from the extracts left a red, oily semisolid, which was purified by being dissolved in dichloromethane and being applied to a thick layer silica gel chromatography plate. An ultraviolet absorbing substance separated as a pale yellow oil. This was determined to be pure by thin layer chromatography. The infrared and nuclear magnetic resonance spectra were in agreement with that expected for the structural formula.

Workup

  1. customequipped with a nitrogen gas inlet, magnetic stirrer
  2. temperaturereflux
  3. additioncondenser, and powder addition funnel
  4. temperatureto maintain
  5. customa vigorous exothermic reaction
  6. stirringStirring of the reaction mixture at room temperature
  7. additionafter the addition
  8. temperaturemaintaining the nitrogen atmosphere
  9. additionwas added dropwise
  10. customrose from 25° C. to 30° C
  11. additionUpon completion of the addition
  12. stirringstirring
  13. customreturned to 25° C
  14. customresulting in formation of a black solid
  15. customrose to around 50° C
  16. stirringStirring
  17. customreturned to 25° C
  18. customThe black solid was removed by filtration
  19. washwashed with ethanol
  20. concentrationThe filtrate was concentrated in a rotary evaporator
  21. additiondiluted with about an equal volume of water
  22. filtrationfiltered through a Celite® pad
  23. extractionExtraction
  24. customwith diethyl ether and removal of the ether from the extracts
  25. waitleft a red, oily semisolid, which
  26. customwas purified
  27. dissolutionby being dissolved in dichloromethane
  28. customAn ultraviolet absorbing substance
  29. customseparated as a pale yellow oil

Sources & evidence

ORD record
ord-061c5b4d679d4b889550390aba6c9802
Source dataset
uspto-grants-1987_04
Patent number
US04661438

Reaction notes

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