Potassium Nitrate → 5'-chloro-N-ethyl-4'-fluoro-2'-nitroacetanilide

HRID 1974618Notes

Reaction equation

HRID 1974618 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[F:14])[N:5]([CH2:9][CH3:10])[C:6](=[O:8])[CH3:7].[N+:15]([O-])([O-:17])=[O:16].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:13]([F:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:4]([CH:3]=1)[N:5]([CH2:9][CH3:10])[C:6](=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 15751479N-(3-Chloro-4-fluorophenyl)-N-ethylacetamide

Product 1

HCID 157514805'-chloro-N-ethyl-4'-fluoro-2'-nitroacetanilideYield 61,319.602%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

3'-Chloro-N-ethyl-4'-fluoroacetanilide (101 g, 0.468 mmol) is dissolved in conc. sulfuric acid (300 ml). A solution of potassium nitrate (57 g, 0.564 mol) in conc. sulfuric acid (220 ml) is added dropwise thereto at 5°. The solution obtained is stirred overnight, then poured on to ice/water and extracted with ethyl acetate (2×200 ml). The organic phase is washed in succession with water (200 ml), saturated sodium bicarbonate solution (100 ml) and saturated sodium chloride solution (100 ml). The organic phase is treated with active charcoal, filtered and dried over magnesium sulfate. The solvent is distilled off and the residue is recrystallized from ether/n-hexane. There are obtained 74.8 g (61%) of 5'-chloro-N-ethyl-4'-fluoro-2'-nitroacetanilide with a m.p. of 68°.

Workup

  1. customat 5°
  2. customThe solution obtained
  3. extractionextracted with ethyl acetate (2×200 ml)
  4. washThe organic phase is washed in succession with water (200 ml), saturated sodium bicarbonate solution (100 ml) and saturated sodium chloride solution (100 ml)
  5. additionThe organic phase is treated with active charcoal
  6. filtrationfiltered
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent is distilled off
  9. customthe residue is recrystallized from ether/n-hexane

Sources & evidence

ORD record
ord-972a273813894deca7e3f8fc1fde8198
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

Loading…