Nitric Acid → N-[4-Chloro-2-nitro-5-(trifluoromethyl)phenyl]acetamide

HRID 439500

Reaction equation

HRID 439500 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:8]([Cl:11])=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12]([F:15])([F:13])[F:14])[C:8]([Cl:11])=[CH:9][C:10]=1[N+:16]([O-:18])=[O:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 67676n-[4-Chloro-3-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 22318004N-[4-Chloro-2-nitro-5-(trifluoromethyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To 3-acetamido-6-chlorobenzotrifluoride (908 mg, 3.82 mmol) in concentrated H2SO4 (4 mL) at 0° C. was added dropwise 70% HNO3 (0.5 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature 3 h, and it was poured into ice water (15 g). The precipitate was collected by filtration, affording 990 mg (91%) of crude 3-acetamido-6-chloro-4-nitrobenzofluoride. It was crystallized. from EtOH/H2O to give 770 mg of pure compound as yellow needles. 1H NMR (CDCl3): δ2.326 (s, 3H), 8.345 (s, 1H), 9.293 (s, 1H), 10.222 (s, 1H).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customaffording 990 mg (91%) of crude 3-acetamido-6-chloro-4-nitrobenzofluoride
  3. customIt was crystallized

Sources & evidence

ORD record
ord-8c23bc00c6aa48a0b4e4a2e0bb11dcec
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Linked notes

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