Allyl Alcohol → HCID 14624408, compound

HRID 1650771Notes

Reaction equation

HRID 1650771 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[H-].[Na+].Cl[CH2:8][C:9]1[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=2[Cl:22])[N:12]=[C:11]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:10]=1>C(OCC)(=O)C>[C:23]([C:11]1[N:10]=[C:9]([CH2:8][O:4][CH2:1][CH:2]=[CH2:3])[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=2[Cl:22])[N:12]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 14624390HCID 14624390, compound

Product 1

HCID 14624408HCID 14624408, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 20 ml of allyl alcohol, 0.4 g (0.008 mol) of 50% sodium hydride was added, and the mixture was stirred at room temperature for 30 minutes. Then, 2.8 g (0.008 mol) of 5-chloromethyl-3-(tert-butyl)-1-(2,4,6-trichlorophenyl)-1H-1,2,4-triazole was gradually added thereto under stirring at room temperature. After completion of the dropwise addition, the solution was heated and stirred under reflux for 2 hours. Then, 50 ml of ethyl acetate was added thereto, and the mixture was washed with water. The organic layer was dried, and the solvent was distilled off. The oily substance thereby obtained was purified by silica gel column chromatography to obtain 1.8 g (yield: 60.0%) of the desired compound as pale yellow prismatic crystals. Melting point: 34°-37° C.

Workup

  1. stirringunder stirring at room temperature
  2. additionAfter completion of the dropwise addition
  3. temperaturethe solution was heated
  4. stirringstirred
  5. temperatureunder reflux for 2 hours
  6. washthe mixture was washed with water
  7. customThe organic layer was dried
  8. distillationthe solvent was distilled off
  9. customThe oily substance thereby obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-04df105e08a140ed8b390c11a388c95d
Source dataset
uspto-grants-1990_05
Patent number
US04925864

Reaction notes

Loading…