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

HRID 1731310Notes

Reaction equation

HRID 1731310 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 mol) of 2-chloromethyl-2-(4-chlorophenoxymethyl)-oxirane are added dropwise to a mixture of 13.6 g (0.2 mol) of 1,2,4-triazole and 13.8 g (0.1 mol) of potassium carbonate in 200 ml of acetone, whilst stirring. The mixture is stirred at room temperature for 15 hours and then under reflux for 22 hours. Thereafter, the reaction mixture is 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 chromatographically (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 mixture is stirred at room temperature for 15 hours
  2. temperatureunder reflux for 22 hours
  3. filtrationThereafter, the reaction mixture is 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 chromatographically (silica gel 60 Merck, chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-312f8b8554c248898d66026d6d8f0ff5
Source dataset
uspto-grants-1986_11
Patent number
US04621095

Reaction notes

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