HCID 20571053, compound → HCID 3061545, compound

HRID 1577525Notes

Reaction equation

HRID 1577525 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Sn](CCCC)CCCC)CCC.Cl[C:20]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])([CH3:23])[CH:21]=[O:22]>C1(C)C=CC=CC=1>[O:22]1[C:20]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])([CH3:23])[CH:21]1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 20571053HCID 20571053, compoundHCID 69256052HCID 69256052, compound

Product 1

HCID 3061545HCID 3061545, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tri-n-butyltin imidazole (9.28 g), 2-chloro-2-(2,4-dichlorophenyl)propionaldehyde (4.75 g) and toluene (100 ml) was heated under reflux for 5 hours. After cooling, the reaction mixture was washed with water, dried over anhydrous magnesium sulfate and evaporated to remove the solvent. The oily residue was purified by chromatography over silica gel to give 1-[1,2-epoxy-2-(2,4-dichlorophenyl)propyl]imidazole (2.35 g, yield 43.7%) as an oil. The product was dissolved in ether, and the ether solution was neutralized by adding fuming nitric acid to give crystals of 1-[1,2-epoxy-2-(2,4-dichlorophenyl)propyl]-imidazole nitrate, which were recrystallized from methanol.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto remove the solvent
  8. customThe oily residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-9c5e322de6254e28b753b2dd200670fd
Source dataset
uspto-grants-1981_09
Patent number
US04288448

Reaction notes

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