Nitric Acid → HCID 18509292, compound

HRID 1356640Notes

Reaction equation

HRID 1356640 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[N+:20]([O-])([OH:22])=[O:21].O.C(OCC)C>C(O)(=O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 18509328HCID 18509328, compound

Product 1

HCID 18509292HCID 18509292, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4′-Fluoro-N-methyl-p-toluenesulfonanilide (1.00 g (3.58 mmol) was dissolved in 5.0 ml of acetic acid. To this, was added with stirring at room temperature, 97% fuming nitric acid (0.35 ml (8.19 mmol)) dropwise, and the mixture was stirred at 100° C. for one hour, poured into water and extracted with ethyl acetate. The extract was washed with saturated aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give crude crystals. Diethyl ether was added to these crystals. The crystals were filtered and washed to give 0.81 g (70%) of the title compound as yellow crystals.

Workup

  1. additionTo this, was added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crude crystals
  7. filtrationThe crystals were filtered
  8. washwashed

Sources & evidence

ORD record
ord-c96b93068e20455bbcd0c9a2ca542199
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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