Propionic anhydride → HCID 15580732, compound

HRID 543819Notes

Reaction equation

HRID 543819 reaction equation
F[C:2](F)(F)[C:3]([NH:5][C:6]1[CH2:10][CH:9]([CH3:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15](C(=O)C(F)(F)F)=[CH:14][CH:13]=2)[N:7]=1)=[O:4].[C:26](OC(=O)CC)(=O)CC>O>[CH3:11][CH:9]1[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][CH3:26])[CH2:10]1

Participants

4

Reactant 2

HCID 31263Propionic anhydrideHCID 15580702HCID 15580702, compound

Product 1

HCID 15580732HCID 15580732, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g. of 3-amino-5-methyl-1-phenyl-2-pyrazoline (prepared in Example 5) and 25.0 ml. of propionic anhydride is allowed to remain at room temperature for 16 hours. The reaction mixture is poured into water to separate an oil which crystallizes. The solid is collected by filtration and dissolved in dichloromethane. The solution is passed through a short column of a hydrous magnesium silicate. The effluent is heated at reflux and hexane is added. The first heavy precipitate (purple color) is discarded. The solution is cooled and the ensuing precipitate is collected by filtration. The solid is again dissolved in dichloromethane, columnized and recrystallized with hexane to give 2.3 g. of the product of the Example as plates, m.p. 96.0°-96.5° C.

Workup

  1. additionA mixture of 5.0 g
  2. customto separate an oil which
  3. customcrystallizes
  4. filtrationThe solid is collected by filtration
  5. dissolutiondissolved in dichloromethane
  6. temperatureThe effluent is heated
  7. temperatureat reflux
  8. additionhexane is added
  9. temperatureThe solution is cooled
  10. filtrationthe ensuing precipitate is collected by filtration
  11. dissolutionThe solid is again dissolved in dichloromethane
  12. customrecrystallized with hexane
  13. customto give 2.3 g

Sources & evidence

ORD record
ord-f5d030dcf546497cbb417f7605894de7
Source dataset
uspto-grants-1984_05
Patent number
US04447442

Reaction notes

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