Sulfuric Acid → 4'-Iodo-3'-trifluoromethylisobutyranilide

HRID 614294Notes

Reaction equation

HRID 614294 reaction equation
N[C:2]1[CH:13]=[CH:12][C:5]([NH:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:27].[K+]>O.C(O)(=O)C>[I:27][C:2]1[CH:13]=[CH:12][C:5]([NH:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 16776651N-[4-Amino-3-(trifluoromethyl)phenyl]-2-methylpropanamideHCID 23668193Sodium Nitrite

Product 1

HCID 213122904'-Iodo-3'-trifluoromethylisobutyranilide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

To a solution of 23.0 g. of 4'-amino-3'-trifluoromethylisobutyranilide in 150 ml. of glacial acetic acid and 100 ml. of water, while maintaining the mixture temperature at 10°-20° C., slowly add 17 ml. of concentrated sulfuric acid, cool the resulting mixture to about 0° C. and slowly add 8.5 g. of sodium nitrite in 15 ml. of water maintaining the temperature of the reaction at about 0° C. for 30 minutes. Add 50 g. of potassium iodide in 150 ml. of water and stir the resulting mixture for 1 hour. Filter, water-wash and dissolve the precipitate in 200 ml. of ether and remove the iodine by washing with a 10% sodium sulfite solution. Dry, remove the solvent, and recrystallize from carbon tetrachloride, obtaining the compound of this example, m.p. 143°-145° C.

Workup

  1. additionAdd 50 g
  2. filtrationFilter
  3. washwater-wash
  4. dissolutiondissolve the precipitate in 200 ml
  5. customof ether and remove the iodine
  6. washby washing with a 10% sodium sulfite solution
  7. customDry
  8. customremove the solvent
  9. customrecrystallize from carbon tetrachloride
  10. customobtaining the compound of this example, m.p. 143°-145° C.

Sources & evidence

ORD record
ord-6ebfb8286c674e6ab2a8210a582a146b
Source dataset
uspto-grants-1979_03
Patent number
US04144270

Reaction notes

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