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

HRID 649521Notes

Reaction equation

HRID 649521 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 temperature 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 temperature 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-ffc512e94c4849439a3655f56d0f99c0
Source dataset
uspto-grants-1988_04
Patent number
US04740516

Reaction notes

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