Hydrochloric Acid → HCID 18366183, compound

HRID 342382Notes

Reaction equation

HRID 342382 reaction equation
N([O-])=O.[Na+].[F:5][C:6]([F:18])([O:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1N)[CH:7]([F:9])[F:8].[ClH:19].[S:20](=[O:22])=[O:21]>O.C(O)(=O)C>[F:5][C:6]([F:18])([O:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[S:20]([Cl:19])(=[O:22])=[O:21])[CH:7]([F:9])[F:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 27784342-(1,1,2,2-tetrafluoroethoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 18366183HCID 18366183, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution containing 3.8 g (55 mmol) of sodium nitrite in 6 mL of water was added slowly with cooling and stirring to a mixture of 12.3 g (50 mmol) of 2-(1,1,2,2-tetrafluoroethoxy)aniline, 18 mL of concentrated aqueous hydrochloric acid, and 5 mL of acetic acid that was precooled to -10° C. After 45 min, the resulting mixture was added in portions to a -10° C. solution of 1.3 g (18 mmol) of cuprous chloride and 0.5 g (4 mmol) of cupric chloride in 50 mL of acetic acid saturated with sulfur dioxide (more than 12 g). The mixture was then warmed to ambient temperature and stirred for 90 min after which it was poured onto ice. The mixture obtained was extracted with diethyl ether and the extract was washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate. The fractions containing product were combined and concentrated by evaporation under reduced pressure to obtain 11.0 g (75 percent of theory) of the title compound as a yellow oil. NMR: 1H (CDCl3): 8.07(dd, 1H, J=1.7, 8.0), 7.76(ddd, 1H, J=1.7, 7.8, 8.1), 7.59(dd, 1H, J=1.2, 8.1), 7.45(ddd, 1H, J=1.2, 7.8, 8.0), 6.05(tt, 1H, J=4.0, 53.0). The mass spectrum had a parent peak M+ 292.

Workup

  1. additionwas added slowly
  2. temperaturewith cooling
  3. customwas precooled to -10° C
  4. additionwas poured onto ice
  5. customThe mixture obtained
  6. extractionwas extracted with diethyl ether
  7. washthe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. customThe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate
  11. additionThe fractions containing product
  12. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3e930e7c80ac4d99a51899c5bb09392a
Source dataset
uspto-grants-1999_01
Patent number
US05858924

Reaction notes

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