Water → 1-[2-(2,4-Dichlorophenyl)hexyl]-4-nitro-1H-imidazole

HRID 1732397Notes

Reaction equation

HRID 1732397 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)([O-:5])=[O:4].CS(O[CH2:16][CH:17]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[CH2:18][CH2:19][CH2:20][CH3:21])(=O)=O.O>CO>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[CH:17]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][N:9]1[CH:10]=[C:6]([N+:3]([O-:5])=[O:4])[N:7]=[CH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 19775615HCID 19775615, compoundHCID 178526856HCID 178526856, compound

Product 1

HCID 203061261-[2-(2,4-Dichlorophenyl)hexyl]-4-nitro-1H-imidazoleYield 106.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1.3 g (0.0307 mole) of sodium hydroxide in 150 ml of methanol is added 3.5 g (0.0307 mole) of 4-nitroimidazole, and the solution is heated and the methanol distilled off. To the concentrate is added 100 ml of dimethyl formamide and the solution is heated up to 120° to remove the excess methanol and water. This dimethyl formamide solution is then cooled to less than 90° and 10.0 g (of 0.0307 mole) of 2-(2,4-dichlorophenyl)hexyl methane sulfonate is added. The reaction mixture is heated up to 145° for two hours and then cooled and poured into water. The organic material is extracted out with ether and after drying, the extract is stripped to give 11.2 g of residue. The concentrate is triturated with hexane and then dissolved in 25 ml of methanol. The methanol solution is poured slowly into water and a gummy solid forms. This solid is separated by filtration, dried and recrystallized from acetone-hexane to give 4.2 g (41 %) of the product, m.p. 67°-9°.

Workup

  1. temperaturethe solution is heated
  2. distillationthe methanol distilled off
  3. additionTo the concentrate is added 100 ml of dimethyl formamide
  4. temperaturethe solution is heated up to 120°
  5. customto remove the excess methanol and water
  6. temperatureThis dimethyl formamide solution is then cooled to less than 90°
  7. temperatureThe reaction mixture is heated up to 145° for two hours
  8. temperaturecooled
  9. extractionThe organic material is extracted out with ether
  10. customafter drying

Sources & evidence

ORD record
ord-fcaadb2acaaa43d08b79d8465280372e
Source dataset
uspto-grants-1980_12
Patent number
US04237158

Reaction notes

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