Nitric Acid → HCID 178526854, compound

HRID 1769293Notes

Reaction equation

HRID 1769293 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[NH:14][CH:15]=[CH:16][N:17]=1.[N+:18]([O-])([OH:20])=[O:19].S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[NH:17][CH:16]=[C:15]([N+:18]([O-:20])=[O:19])[N:14]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 18947716HCID 18947716, compound

Product 1

HCID 178526854HCID 178526854, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(2,6-dichloro-4-trifluoromethylphenyl)-imidazole (5.62 g, 0.02 mol), nitric acid (70% w/w, 5.6 ml) and sulphuric acid (98% w/w, 5.6 ml) was strirred and heated at 70° C. for a total of 51 hours. After cooling the ceaction mixture was poured into a mixture of ice and water (approximately 75 ml) and the precipitated solid was filtered off. It was purified by mplc on silica eluted with a mixture of ethyl acetate and dichloromethane (1:20) to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-nitroimidazole (4.21g), m.p. 254°-255° C., as a cream crystalline solid.

Workup

  1. temperatureAfter cooling the ceaction mixture
  2. filtrationthe precipitated solid was filtered off
  3. customIt was purified by mplc on silica
  4. washeluted with a mixture of ethyl acetate and dichloromethane (1:20)

Sources & evidence

ORD record
ord-8aad7afd3411406695edf852b3a17d9f
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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