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

HRID 2419339Notes

Reaction equation

HRID 2419339 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 1.3g (0.0307 mole) of sodium hydroxide in 150 ml of methanol is added 3.5g (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 10.0g (of 0.0307 mole) of 2-(2,4-dichlorophenyl)hexyl methane sulfonate is added. The reaction mixture is heated up to 145° for 2 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 11.2g 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 4.2g (41%) of the product, m.p. 67°-69°.

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 2 hours
  8. temperaturecooled
  9. extractionThe organic material is extracted out with ether
  10. customafter drying

Sources & evidence

ORD record
ord-5b2bf18bd5594e9c94525d7b8a993869
Source dataset
uspto-grants-1978_08
Patent number
US04105762

Reaction notes

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