Benzene → HCID 70506358, compound

HRID 280547Notes

Reaction equation

HRID 280547 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:7][C:8]1[CH:31]=[CH:30][C:11]([C:12]([C:14]2[CH2:15][C:16]([F:29])([CH:26]=[CH:27][N:28]=2)[C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])=[O:13])=[CH:10][CH:9]=1.[CH2:32]([OH:34])[CH3:33].[CH:35]1C=CC=C[CH:36]=1>>[CH2:35]([O:18][C:17]([O:34][CH2:32][CH3:33])([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:16]1([F:29])[CH:26]=[CH:27][N:28]=[C:14]([C:12](=[O:13])[C:11]2[CH:10]=[CH:9][C:8]([Cl:7])=[CH:31][CH:30]=2)[CH2:15]1)[CH3:36]

Participants

5

Reactant 4

HCID 241BenzeneHCID 702EthanolHCID 24819Phosphorus pentachlorideHCID 70457210HCID 70457210, compound

Product 1

HCID 70506358HCID 70506358, compoundYield 75%

Procedure

To a mixture of phosphorus pentachloride (7.3 g) in benzene (250 ml), 2-(4-chlorobenzoyl)-4-fluoro-isonicotinanilide (12 g) was added, and the mixture was refluxed for 2 hours under stirring. After cooling, the solvent was completely distilled off under vacuum. The resulting residue was gradually added to an ethyl alcohol solution of potassium hydroxide (3.7 g) and allowed to react at room temperature over a period of 2 hours. After completion of the reaction, ethyl alcohol was distilled off under vacuum. The resulting residue was extracted, after addition of water, with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate. Thereafter, the ethyl acetate was distilled off under vacuum. Upon recrystallizing the resulting residue with a mixed solvent of ethyl acetate and n-hexane, the titled compound was obtained in an amount of 10.7 g (yield: 75%). m.p. 96°-97° C.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 2 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was completely distilled off under vacuum
  5. additionThe resulting residue was gradually added to an ethyl alcohol solution of potassium hydroxide (3.7 g)
  6. customto react at room temperature over a period of 2 hours
  7. distillationwas distilled off under vacuum
  8. extractionThe resulting residue was extracted
  9. additionafter addition of water
  10. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  11. distillationThereafter, the ethyl acetate was distilled off under vacuum
  12. customUpon recrystallizing the resulting residue with a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-53c5596b97ba473ca05867e0f2481c04
Source dataset
uspto-grants-1986_05
Patent number
US04590198

Reaction notes

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