Propionic anhydride → HCID 15580734, compound

HRID 543823Notes

Reaction equation

HRID 543823 reaction equation
F[C:2](F)(F)[C:3]([NH:5][C:6]1[CH2:10][CH:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[N:8]([C:18]2[CH:23]=[CH:22][C:21](C(=O)C(F)(F)F)=[CH:20][CH:19]=2)[N:7]=1)=[O:4].[C:32](OC(=O)CC)(=O)CC>CN(C)C1C=CN=CC=1.O>[C:18]1([N:8]2[CH:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)[CH2:10][C:6]([NH:5][C:3](=[O:4])[CH2:2][CH3:32])=[N:7]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 31263Propionic anhydrideHCID 15580706HCID 15580706, compound

Product 1

HCID 15580734HCID 15580734, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 4.5 g. of 3-amino-1-phenyl-5-p-tolyl-2-pyrazoline (prepared in Example 3), 20.0 ml. of propionic anhydride and 200 mg. of 4-dimethylaminopyridine is heated on a steam bath for 2 hours. The reaction mixture is cooled to room temperature then water is added to separate a solid. The solid is collected then is dissolved in dichloromethane. The solution is passed through a short column of a hydrous magnesium silicate. The effluent is heated to reflux and hexane is added until turbidity appears. The mixture is cooled and filtered to collect a solid. The solid is recrystallized again from 80% ethanol. This material is dissolved in 100 ml. of methanol, then 200 mg. of potassium carbonate is added and the mixture is refluxed for 15 minutes. Water is added until turbidity appears. The mixture is cooled and filtered to collect the solid. The solid is dissolved in dichloromethane. This solution is columnized and recrystallized as described above to yield 2.4 g. of the desired product as colorless needles, m.p. 123.5°-125° C.

Workup

  1. additionA mixture of 4.5 g
  2. customto separate a solid
  3. customThe solid is collected
  4. dissolutionthen is dissolved in dichloromethane
  5. temperatureThe effluent is heated
  6. temperatureto reflux
  7. additionhexane is added until turbidity
  8. temperatureThe mixture is cooled
  9. filtrationfiltered
  10. customto collect a solid
  11. customThe solid is recrystallized again from 80% ethanol
  12. dissolutionThis material is dissolved in 100 ml
  13. additionof potassium carbonate is added
  14. temperaturethe mixture is refluxed for 15 minutes
  15. additionWater is added until turbidity
  16. temperatureThe mixture is cooled
  17. filtrationfiltered
  18. customto collect the solid
  19. dissolutionThe solid is dissolved in dichloromethane
  20. customrecrystallized
  21. customto yield 2.4 g

Sources & evidence

ORD record
ord-3c2c0b3f007e47be9f2c50d0e3fbb8e2
Source dataset
uspto-grants-1984_05
Patent number
US04447442

Reaction notes

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