Hydrochloric Acid → N-(1,2-Diethylpyrazolidin-4-yl)-4-fluorobenzamide

HRID 1706397Notes

Reaction equation

HRID 1706397 reaction equation
C(O)(=O)/C=C\C(O)=O.[CH2:9]([N:11]1[CH2:15][CH:14]([N:16]2C(=O)[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])[CH2:13][N:12]1[CH2:27][CH3:28])[CH3:10].Cl.[F:30]C1C=CC(C(Cl)=O)=CC=1>>[F:30][C:23]1[CH:22]=[CH:19][C:18]([C:17]([NH:16][CH:14]2[CH2:15][N:11]([CH2:9][CH3:10])[N:12]([CH2:27][CH3:28])[CH2:13]2)=[O:26])=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 678794-Fluorobenzoyl chlorideHCID 70058803HCID 70058803, compound

Product 1

HCID 13746889N-(1,2-Diethylpyrazolidin-4-yl)-4-fluorobenzamide

Procedure

A solution of 10 g. (0.026 mole) of 1,2-diethyl-4-phthalimidopyrazolidine maleate in 25 ml. of 6 N hydrochloric acid was refluxed two hours, the resulting mixture was cooled and filtered. The filter cake was washed with water which was combined with the acidic solution. The acidic solution was made basic with dilute sodium hydroxide and cooled with ice. To the resulting solution was added 8.2 g. (0.052 mole) of p-fluorobenzoyl chloride and the mixture shaken for 10 minutes. The resulting mixture was extracted with chloroform, the chloroform diluted with an equal volume of isopropyl ether and the resulting solution extracted with dilute hydrochloric acid. The acid layer was made basic with dilute sodium hydroxide and extracted with chloroform. The chloroform was dried (sodium sulfate) and concentrated. The residue was crystallized from isooctaneisopropyl ether and recrystallized from isooctaneisopropyl ether containing a few drops of ethyl acetate and clarified by charcoal treatment. The product (2.0 g; 29%) melted at 114°-116° C.

Workup

  1. temperaturethe resulting mixture was cooled
  2. filtrationfiltered
  3. washThe filter cake was washed with water which
  4. temperaturecooled with ice
  5. additionTo the resulting solution was added 8.2 g
  6. extractionThe resulting mixture was extracted with chloroform
  7. additionthe chloroform diluted with an equal volume of isopropyl ether
  8. extractionthe resulting solution extracted with dilute hydrochloric acid
  9. extractionextracted with chloroform
  10. dry with materialThe chloroform was dried (sodium sulfate)
  11. concentrationconcentrated
  12. customThe residue was crystallized from isooctaneisopropyl ether
  13. customrecrystallized from isooctaneisopropyl ether containing a few drops of ethyl acetate

Sources & evidence

ORD record
ord-9e4b67214cce43bba07ffe971dd8cd55
Source dataset
uspto-grants-1980_06
Patent number
US04207327

Reaction notes

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