Iodoethane → 1-Ethoxy-4-nitro-2,6-bis(trifluoromethyl)-1H-benzimidazole

HRID 1576378Notes

Reaction equation

HRID 1576378 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[N:4]=[C:3]1[C:18]([F:21])([F:20])[F:19].[CH2:22](I)[CH3:23].[O-]CC.[Na+]>CO>[CH2:22]([O:1][N:2]1[C:6]2[CH:7]=[C:8]([C:14]([F:15])([F:16])[F:17])[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[N:4]=[C:3]1[C:18]([F:19])([F:21])[F:20])[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2723922Sodium ethoxideHCID 229087364-Nitro-2,6-bis(trifluoromethyl)-1H-benzimidazol-1-ol

Product 1

HCID 215124081-Ethoxy-4-nitro-2,6-bis(trifluoromethyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 6 g. portion of 1-hydroxy-4-nitro-2,6-bis(trifluoromethyl)benzimidazole was mixed with 50 ml. of methanol, 10 ml. of ethyl iodide, and 2.5 g. of sodium ethoxide. The mixture was heated at reflux temperature overnight with stirring, and was then cooled and evaporated to dryness. The residue was taken up in ether, and the ether solution was washed with water. The ether layer was then evaporated to dryness, and the residue was recrystallized from petroleum ether to produce the desired 1-ethoxy-4-nitro-2,6-bis(trifluoromethyl)benzimidazole, m.p. 94°-96°C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature overnight
  3. temperaturewas then cooled
  4. customevaporated to dryness
  5. washthe ether solution was washed with water
  6. customThe ether layer was then evaporated to dryness
  7. customthe residue was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-d648e96f25ce4dafb40f1edffe2c25e1
Source dataset
uspto-grants-1976_09
Patent number
US03980784

Reaction notes

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