Isobutyryl chloride → Flutamide

HRID 971859

Reaction equation

HRID 971859 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-:3])=[O:2].[C:15](Cl)(=[O:19])[CH:16]([CH3:18])[CH3:17]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])=[CH:6][C:5]=1[C:11]([F:12])([F:13])[F:14])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 949554-Nitro-3-(trifluoromethyl)aniline

Product 1

HCID 3397Flutamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred, cooled solution of 100 g. of 4-nitro-3-trifluoromethylaniline in 400 ml. of pyridine, slowly and in a dropwise fashion, add 54 g. of isobutyrylchoride and then heat the reaction mixture on a steam bath for 1.5 hours. Cool and pour the resulting mixture into ice-water, filter and water-wash the crude anilide, crystallize the product of this example from benzene to obtain analytically pure material, m.p. 111.5°-112.5° C.

Workup

  1. temperatureTo a stirred, cooled solution of 100 g
  2. temperatureCool
  3. filtrationfilter
  4. washwater-wash the crude anilide
  5. customcrystallize the product of this example from benzene
  6. customto obtain analytically pure material, m.p. 111.5°-112.5° C.

Sources & evidence

ORD record
ord-18d44c48ee8a46d2983e94d746bfccfb
Source dataset
uspto-grants-1979_07
Patent number
US04161540

Linked notes

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