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

HRID 979455Notes

Reaction equation

HRID 979455 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

Participants

5

Reactant 3

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

Product 1

HCID 13295576HCID 13295576, compound

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 with stirring. The mixture is allowed to stir at room temperature for 15 hours and then under reflux for 22 hours. The reaction mixture is then filtered cold and the filtrate is evaporated 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. are obtained.

Workup

  1. stirringto stir at room temperature for 15 hours
  2. temperatureunder reflux for 22 hours
  3. filtrationThe reaction mixture is then filtered cold
  4. customthe filtrate is evaporated 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-73a01b4204e246e19ecf4994f7a2d524
Source dataset
uspto-grants-1987_05
Patent number
US04668660

Reaction notes

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