Trifluoroacetic acid → HCID 11087198, compound

HRID 1463273Notes

Reaction equation

HRID 1463273 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1([CH3:15])[CH2:9][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[O:5]1.[N+:18]([O-])([O-:20])=[O:19].[NH4+].FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1([CH3:15])[CH2:9][C:8](=[O:10])[C:7]2[CH:11]=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=[CH:14][C:6]=2[O:5]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 22985Ammonium nitrateHCID 18987747HCID 18987747, compound

Product 1

HCID 11087198HCID 11087198, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 15 ml of chloroform were dissolved 1.99 (8.1 mmole) of the compound obtained in step 1 and 0.64(8.1 mmole) of ammonium nitrate; and, 4.5 ml (32 mmole) of anhydrous trifluoroacetic acid was added thereto at room temperature. The resultant mixture was stirred at room temperature for 3 hours; and, the reaction was terminated with a saturated NaHCO3 aqueous solution. The resultant solution was extracted with dichloromethane (50 ml×2), washed with 50 ml of water and with 20 ml of saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain residue, which was purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (4:1) as an eluent to obtain 1.24 g (yield 55%) of the title compound.

Workup

  1. customat room temperature
  2. customand, the reaction was terminated with a saturated NaHCO3 aqueous solution
  3. extractionThe resultant solution was extracted with dichloromethane (50 ml×2)
  4. washwashed with 50 ml of water and with 20 ml of saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain residue, which
  9. customwas purified by silica gel column chromatography
  10. additiona mixture of hexane and ethyl acetate (4:1) as an eluent

Sources & evidence

ORD record
ord-55a66fee95494b2faf1dc0b16d498662
Source dataset
uspto-grants-1994_04
Patent number
US05300511

Reaction notes

Loading…