Propionic anhydride → HCID 15580733, compound

HRID 543822Notes

Reaction equation

HRID 543822 reaction equation
FC(F)(F)[C:3]([NH:5][C:6]1[CH2:10][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:17]2[CH:22]=[CH:21][C:20](C(=O)C(F)(F)F)=[CH:19][CH:18]=2)[N:7]=1)=[O:4].[C:31](OC(=O)CC)(=O)[CH2:32]C>CN(C)C1C=CN=CC=1.O>[C:17]1([N:8]2[CH:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][C:6]([NH:5][C:3](=[O:4])[CH2:31][CH3:32])=[N:7]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 31263Propionic anhydrideHCID 15580705HCID 15580705, compound

Product 1

HCID 15580733HCID 15580733, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 10.0 g. of 3-amino-1,5-diphenyl-2-pyrazoline (prepared in Example 4), 30.0 ml. of propionic anhydride and 500 mg. of 4-dimethylaminopyridine is heated on a steam bath for 3 hours. The mixture is poured into water to separate an oil. The oil crystallizes and the solid is collected by filtration. The solid is dissolved in dichloromethane. The solution is dried over anhydrous sodium sulfate then is columnized and recrystallized twice as for Example 26 (A) to give 6.0 g. of the product of the Example as colorless plates, m.p. 148.0-148.5° C.

Workup

  1. additionA mixture of 10.0 g
  2. customto separate an oil
  3. customThe oil crystallizes
  4. filtrationthe solid is collected by filtration
  5. dissolutionThe solid is dissolved in dichloromethane
  6. dry with materialThe solution is dried over anhydrous sodium sulfate
  7. customto give 6.0 g

Sources & evidence

ORD record
ord-ffc4c062cdc24eaa8896fcf3dfd6797a
Source dataset
uspto-grants-1984_05
Patent number
US04447442

Reaction notes

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