Nitric Acid → Flutamide

HRID 1155579Notes

Reaction equation

HRID 1155579 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[NH:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9].OS(O)(=O)=O.O=S(=O)=O.[N+:26]([O-])([OH:28])=[O:27]>O>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[N+:26]([O-:28])=[O:27])[NH:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 24681Fuming sulfuric acidHCID 1372643-Trifluoromethylisobutyranilide

Product 1

HCID 3397Flutamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Add portion-wise 57.5 g. of m-trifluoromethyl isobutyranilide to 260 ml. of 15-18% oleum while maintaining the internal temperature at about 5° C. To this mixture add drop-wise 20 g. of 90% nitric acid with stirring. Stir at about 5° C. for 2 hours and pour into about 11/2 liters of ice and water with stirring. Collect the 3'-trifluoromethyl-4'-nitro-isobutyranilide by filtration and wash with water until substantially free of excess acid.

Workup

  1. additionAdd portion-wise 57.5 g
  2. additionTo this mixture add drop-wise 20 g
  3. stirringwith stirring
  4. customCollect the 3'-trifluoromethyl-4'-nitro-isobutyranilide
  5. filtrationby filtration
  6. washwash with water until substantially free of excess acid

Sources & evidence

ORD record
ord-3bb1905416d647b5a51cf2e60bb04d16
Source dataset
uspto-grants-1981_11
Patent number
US04302599

Reaction notes

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