Nitric Acid → 2-(p-Chlorophenyl)-3-Nitro-4-(5-Nitro-2-Thienyl)-5-(Trifluoromethyl)Pyrrol

HRID 2396546Notes

Reaction equation

HRID 2396546 reaction equation
[N+:1]([O-:4])([OH:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15]([C:17]([F:20])([F:19])[F:18])=[C:14]([C:21]3[S:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)[CH:13]=2)=[CH:8][CH:7]=1.O>C(OC(=O)C)(=O)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[NH:16][C:15]([C:17]([F:19])([F:18])[F:20])=[C:14]([C:21]3[S:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)[C:13]=2[N+:1]([O-:4])=[O:3])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 962WaterHCID 194192875-(p-Chlorophenyl)-3-(5-Nitro-2-Thienyl)-2-(Trifluoromethyl)Pyrrole

Product 1

HCID 194192712-(p-Chlorophenyl)-3-Nitro-4-(5-Nitro-2-Thienyl)-5-(Trifluoromethyl)Pyrrol

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A 90% nitric acid solution (0.02 g, 0.28 mmol) is added to a solution of 5-(p-chlorophenyl)-3-(5-nitro-2-thienyl)-2-(trifluoromethyl)pyrrole (0.13 g, 0.34 mmol) in acetic anhydride. The reaction mixture is stirred at room temperature for ten minutes, treated with additional 90% nitric acid solution (0.02 g, 0.28 mmol), stirred at room temperature for 15 minutes, poured into water, stirred at room temperature overnight and extracted with ether. The combined organic extracts are dried over MgSO4 and concentrated in vacuo to obtain the title product as a tan solid which is identified by 1HNMR spectral analysis.

Workup

  1. stirringstirred at room temperature for 15 minutes
  2. stirringstirred at room temperature overnight
  3. extractionextracted with ether
  4. dry with materialThe combined organic extracts are dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-264d8c51f55e48f883aa71a0a1fcd788
Source dataset
uspto-grants-1996_02
Patent number
US05492925

Reaction notes

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