Nitric Acid → N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide

HRID 1846512Notes

Reaction equation

HRID 1846512 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[C:4]([C:12]([F:13])([F:14])[F:15])[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:6]([N+:16]([O-:18])=[O:17])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10560920N-(4-fluoro-2-(trifluoromethyl)phenyl)acetamide

Product 1

HCID 10778132N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

8.80 g (39.7 mmol) N-(4-fluoro-2-trifluoromethyl-phenyl)-acetamide were added to 60 mL 97% sulphuric acid while cooling with ice. 6.60 mL (95.3 mmol) nitric acid were slowly added dropwise to this mixture at 0° C. and with constant stirring. After the addition had ended the mixture was stirred for 30 min at 0° C. Then the cooling was removed and the reaction mixture was stirred for a further 1.5 h to complete the reaction. The reaction mixture was carefully poured onto 500 g ice and stirred for 30 min. The precipitate formed was filtered off, washed with 150 mL water and dried i. vac.

Workup

  1. temperaturewhile cooling with ice
  2. additionAfter the addition
  3. customThen the cooling was removed
  4. stirringthe reaction mixture was stirred for a further 1.5 h
  5. customthe reaction
  6. stirringstirred for 30 min
  7. customThe precipitate formed
  8. filtrationwas filtered off
  9. washwashed with 150 mL water
  10. customdried i

Sources & evidence

ORD record
ord-333410494a534dd8b9e9dd48dddea710
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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