Nitric Acid → HCID 135786513, compound

HRID 1591083Notes

Reaction equation

HRID 1591083 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]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=1.O.[N+:23]([O-])([OH:25])=[O:24]>S(=O)(=O)(O)O>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:7]=[C:2]([Cl:1])[C:3]=1[C:13]1[NH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([C:18]([F:21])([F:19])[F:20])[N:17]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 178506193HCID 178506193, compound

Product 1

HCID 135786513HCID 135786513, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylimidazole (1.0 g, 0.0027 mol) in fuming nitric acid (95%, 1 ml) and fuming sulphuric acid (30% free SO3, 1 ml) was stirred and heated at 120° C. for 3.5 hours. The mixture was poured into cold water (50 ml) and the solid was filtered off and washed with water. The resultant solid was purified by chromatography on silica gel, eluting with a mixture of ethyl acetate and n-hexane (1:5) to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-5-nitro 4-trifluoromethylimidazole (0.7 g) as an off-white solid, m.p. 244°-252° C.

Workup

  1. filtrationthe solid was filtered off
  2. washwashed with water
  3. customThe resultant solid was purified by chromatography on silica gel
  4. washeluting with a mixture of ethyl acetate and n-hexane (1:5)

Sources & evidence

ORD record
ord-5ee7c64f4f1a415dba482b18b637482b
Source dataset
uspto-grants-1993_04
Patent number
US05206257

Reaction notes

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