Ethanol → 4-Ethoxy-7-nitro-2,5-bis(trifluoromethyl)benzimidazole

HRID 1578719Notes

Reaction equation

HRID 1578719 reaction equation
Cl[C:2]1[C:10]2[NH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7][C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[CH2:22]([OH:24])[CH3:23].[Na]>O>[CH2:22]([O:24][C:2]1[C:10]2[NH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7][C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19])[CH3:23]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 5360545SodiumHCID 1355549354-Chloro-7-nitro-2,5-bis(trifluoromethyl)benzimidazole2×

Product 1

HCID 215585514-Ethoxy-7-nitro-2,5-bis(trifluoromethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-7-nitro-2,5-bis(trifluoromethyl)benzimidazole (3.0 grams; 0.09 mole) was added to about 100 milliliters of ethanol, and the mixture was then refluxed overnight (3.0 grams) and the starting material was recovered. Sodium (.42 gram; 0.018 mole) was added to 100 milliliters of ethanol, and the recovered 4-chloro-7-nitro-2,5-bis(trifluoromethyl)benzimidazole was added at room temperature and the resulting reaction mixture was stirred at room temperature over a weekend. TLC showed only the starting material, so the reaction mixture was heated to reflux and refluxed overnight. The reaction mixture was then poured into water, acidified, and extracted with ethyl acetate. The extract was dried over magnesium sulfate and solvent removed by evaporation to obtain the desired 4-ethoxy-7-nitro-2,5-bis(trifluoromethyl)benzimidazole. After recrystallization from a mixture of ethanol and water, it melted at 144°-46°C. Analysis, Calc.: C, 38.50; H, 2.06; N, 12.24 Found: C, 38.65; H, 2.26; N, 12.36

Workup

  1. temperaturethe mixture was then refluxed overnight (3.0 grams)
  2. customthe starting material was recovered
  3. customthe resulting reaction mixture
  4. temperatureso the reaction mixture was heated
  5. temperatureto reflux
  6. temperaturerefluxed overnight
  7. extractionextracted with ethyl acetate
  8. dry with materialThe extract was dried over magnesium sulfate and solvent
  9. customremoved by evaporation

Sources & evidence

ORD record
ord-8c15f1b4ae7a439ab120cd8648356016
Source dataset
uspto-grants-1976_02
Patent number
US03939166

Reaction notes

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