Hydrochloric Acid → 2-(2,6-Dichloro-4-trifluoromethylphenyl)-imidazole-4,5-dicarboxamide

HRID 1769289Notes

Reaction equation

HRID 1769289 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4](Cl)[C:3]=1[C:13]1[NH:14][C:15]([C:20]#[N:21])=[C:16]([C:18]#[N:19])[N:17]=1.[OH-:22].[K+].[ClH:24].C([OH:27])C>O>[Cl:24][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[C:13]1[NH:14][C:15]([C:20]([NH2:21])=[O:27])=[C:16]([C:18]([NH2:19])=[O:22])[N:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 189476852-(2,6-Dichloro-4-trifluoromethylphenyl)-4,5-dicyanoimidazole

Product 1

HCID 189476912-(2,6-Dichloro-4-trifluoromethylphenyl)-imidazole-4,5-dicarboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2-(2,6-dichloro-4-trifluoromethylphenyl)-4,5-dicyanoimidazole (3.3 g, 0.01 mol) and potassium hydroxide (85%, 1.64 g, 0.025 mol) in ethanol (20 ml) and water (2 ml) was heated at reflux for 3.5 hours. After cooling the mixture was poured into water (100 ml) and acidified to pH1 by the addition of concentrated hydrochloric acid. The precipitated solid was filtered off and dried at 80° C. and 10 mm Hg to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-imidazole-4,5-dicarboxamide (0.6 g), m.p. 306°-308° C., as an off white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. temperatureAfter cooling the mixture
  4. filtrationThe precipitated solid was filtered off
  5. customdried at 80° C.

Sources & evidence

ORD record
ord-4b397d69f2904a8e980b692c7fa8959c
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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