Nitric Acid → HCID 135786513, compound

HRID 1769285Notes

Reaction equation

HRID 1769285 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 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 with a mixture of ethyl acetate and n-hexane (1:5)

Sources & evidence

ORD record
ord-49c0095239e54d32941edaf252a2c6f8
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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