Hydrochloric Acid → HCID 3407084, compound

HRID 1586097Notes

Reaction equation

HRID 1586097 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:12]=1[C:13]#[N:14].Cl>CO>[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[C:12]=1[C:13](=[N:2][OH:3])[NH2:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 1456132-Fluoro-6-(trifluoromethyl)benzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3407084HCID 3407084, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 540 ml of methanol was dissolved 58.8 g of hydroxylamine hydrochloride and to the solution was added 160 ml of aqueous solution of sodium carbonate containing 49.4 g thereof. 40 g of 2-fluoro-6-trifluoromethylbenzonitrile was added thereto at room temperature with stirring, and then further stirred 3 hours at 60° C. After removing the solvent methanol by distillation from the solution, the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and it was concentrated under reduced pressure, thereby obtaining crude crystals. The crystals were then added with 200 ml of 3N aqueous solution of hydrochloric acid and thoroughly stirred, then the insoluble substance resulted in the solution was removed by filtration. The filtrate was then neutralized with 10% aqueous solution of sodium hydroxide under cooling and then extracted again with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solution was concentrated under reduced pressure to obtain 26.6 g of the objective compound. m.p. 155-157° C.

Workup

  1. customfurther stirred 3 hours
  2. customat 60° C
  3. customAfter removing the solvent methanol
  4. distillationby distillation from the solution
  5. extractionthe solution was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, and it
  7. concentrationwas concentrated under reduced pressure
  8. customobtaining crude crystals
  9. stirringthoroughly stirred
  10. customthe insoluble substance resulted in the solution
  11. customwas removed by filtration
  12. temperatureunder cooling
  13. extractionextracted again with ethyl acetate
  14. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  15. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5bd2f48abbab4f908d9cc6d4e6ed473a
Source dataset
uspto-grants-1999_08
Patent number
US05942538

Reaction notes

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