1H-1,2,4-Triazole → HCID 13295576, compound

HRID 2290752Notes

Reaction equation

HRID 2290752 reaction equation
Cl[CH2:2][C:3]1([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH2:5][O:4]1.[NH:15]1[CH:19]=[N:18][CH:17]=[N:16]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:3]([OH:4])([CH2:5][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH2:2][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)=[CH:9][CH:10]=1.[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:3]([OH:4])([CH2:5][N:18]2[CH:17]=[N:16][N:15]=[CH:19]2)[CH2:2][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 13295541HCID 13295541, compound

Product 2

HCID 13295576HCID 13295576, compoundYield 43%HCID 13295577HCID 13295577, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

9.4 g (0.04 mole) of 2-chloromethyl-2-(4-chlorophenoxymethyl)-oxirane are added dropwise to a mixture of 13.6 g (0.2 mole) of 1,2,4-triazole and 13.8 g (0.1 mole) of potassium carbonate in 200 ml of acetone, while stirring. The reaction mixture is stirred at room tempereture for 15 hours and then under reflux for 22 hours. It is then filtered cold and the filtrate is concentrated in vacuo. The oily residue is dissolved in chloroform and the solution is washed with water, dried over sodium sulphate and purified by chromatography (silica gel 60 Merck, chloroform/methanol=20/1). 5.8 g (43% of theory) of 2-(4-chlorophenoxymethyl)-1,3-di(1,2,4-triazol-1-yl)-2-hydroxypropane of melting point 99° C. (Example 1) and 2.0 g (15% of theory) of 2-(4-chlorophenoxymethyl)-2-hydroxy-1-(1,2,4-triazol-1-yl)-3-(1,2,4-triazol-4-yl)-propane (Example 2) of melting point 160° C. are obtained.

Workup

  1. stirringThe reaction mixture is stirred at room tempereture for 15 hours
  2. temperatureunder reflux for 22 hours
  3. filtrationIt is then filtered cold
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe oily residue is dissolved in chloroform
  6. washthe solution is washed with water
  7. dry with materialdried over sodium sulphate
  8. custompurified by chromatography (silica gel 60 Merck, chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-540f3f2138df4eaf819469a21b58848e
Source dataset
uspto-grants-1986_10
Patent number
US04618619

Reaction notes

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