Nitric Acid → 2-(p-Chlorophenyl)-5-nitro-3-[(trifluoromethyl)sulfonyl]pyrrole

HRID 1464665Notes

Reaction equation

HRID 1464665 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:4][CH:3]=1.[N+:20]([O-])([OH:22])=[O:21].O>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([N+:20]([O-:22])=[O:21])=[CH:11][C:12]=2[S:13]([C:16]([F:17])([F:19])[F:18])(=[O:14])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 104480682-(p-Chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrrole

Product 1

HCID 189303982-(p-Chlorophenyl)-5-nitro-3-[(trifluoromethyl)sulfonyl]pyrroleYield 37.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2-(p-chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrrole (1.0 g, 0.00323 mol) in acetic anhydride is cooled with an ice bath, treated with nitric acid (0.15 mL, 0.00329 mol), warmed to room temperature, stirred for 20 hours and poured into water. The mixture is decanted and the insolubles are dissolved in ethyl acetate. The ethyl acetate solution is washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an amber residue. Flash chromatography of the residue using silica gel and a 1:1 ethyl acetate/hexanes solution gives the title product as a tan solid (0.43 g, mp 174°-180° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. customThe mixture is decanted
  2. dissolutionthe insolubles are dissolved in ethyl acetate
  3. washThe ethyl acetate solution is washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain an amber residue

Sources & evidence

ORD record
ord-86cd55a4f6ee4dab8a8f72f650c185c6
Source dataset
uspto-grants-1994_04
Patent number
US05306827

Reaction notes

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