Sulfuric Acid → N-(5-Fluoro-2-nitro-4-trifluoromethyl-phenyl)-acetamide

HRID 538201Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:12][C:13](=[O:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].S(=O)(=O)(O)O.[N+:21]([O-])([O-:23])=[O:22].[K+]>>[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:21]([O-:23])=[O:22])=[C:4]([NH:12][C:13](=[O:15])[CH3:14])[CH:3]=1

Participants

Reactant 3

HCID 1118Sulfuric Acid2×

HCID 24434Potassium Nitrate

HCID 10798993N-(3-Fluoro-4-trifluoromethyl-phenyl)-acetamide

Product 1

HCID 10754199N-(5-Fluoro-2-nitro-4-trifluoromethyl-phenyl)-acetamideYield 81.2%

Conditions

Temperature: 0 °C

Procedure

To a vigorously stirred solution of N-(3-fluoro-4-trifluoromethyl-phenyl)-acetamide (0.663 g, 3.00 mmol) and sulfuric acid (3 mL) was added dropwise a solution of potassium nitrate (0.607 g, 6.00 mmol) and conc. sulfuric acid (3 mL) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and then slowly pipetted into ice/water with stirring. The resulting precipitate was collected and dried in vacuo to yield the titled compound (0.648 g, 81% yield) as a single regioisomer. The compound did not yield MS data. 1H NMR (600 MHz, CDCl3): 10.67 (br s, 1H), 8.86 (d, J=12.9 Hz, 1H), 8.57 (d, J=7.2 Hz, 1H), 2.35 (s, 3H).

Workup

stirringwith stirring
customThe resulting precipitate was collected
customdried in vacuo

Sources & evidence

ORD record: ord-dba665522387446387bdc50213aea74f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865713B2

Reaction notes

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