1H-1,2,4-Triazole → HCID 13295580, compound

HRID 649522Notes

Reaction equation

HRID 649522 reaction equation
ClCC1(COC2C=CC(Cl)=CC=2Cl)CO1.[Cl:16][C:17]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:18]=1[O:19][CH2:20][C:21]1([CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[CH2:23][O:22]1.[NH:39]1[CH:43]=[N:42][CH:41]=[N:40]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:16][C:17]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:18]=1[O:19][CH2:20][C:21]([OH:22])([CH2:23][N:39]1[CH:43]=[N:42][CH:41]=[N:40]1)[CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33]

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 13295542HCID 13295542, compoundHCID 13295573HCID 13295573, compound

Product 1

HCID 13295580HCID 13295580, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

23.5 g of a mixture of 2-chloromethyl-2-(2,4-dichlorophenoxymethyl)-oxirane and 2,2-bis(2,4-dichlorophenoxymethyl)-oxirane are added dropwise to a solution of 20.7 g (0.3 mole) of 1,2,4-triazole and 13.8 (0.1 mole) of potassium carbonate in 200 ml of acetone. The reaction mixture is stirred under reflux for 20 hours. It is then filtered cold and the filtrate is concentrated in vacuo. The residue is dissolved in chloroform and the solution is washed with water, dried over sodium sulphate and purified and separated by chromatography (silica gel 60 Merck). Chloroform is first used as the eluting agent. The eluate thereby obtained is concentrated by distilling off the solvent and the residue is stirred with diethyl ether. 4.8 g of 1,3-bis-(2,4-dichlorophenoxy)-2-hydroxy-2-(1,2,4-triazol-1-yl-methyl)-propane (Example 5) of melting point 136° C. are obtained.

Workup

  1. temperatureunder reflux for 20 hours
  2. filtrationIt is then filtered cold
  3. concentrationthe filtrate is concentrated in vacuo
  4. dissolutionThe residue is dissolved in chloroform
  5. washthe solution is washed with water
  6. dry with materialdried over sodium sulphate
  7. custompurified
  8. customseparated by chromatography (silica gel 60 Merck)
  9. customThe eluate thereby obtained
  10. concentrationis concentrated
  11. distillationby distilling off the solvent
  12. stirringthe residue is stirred with diethyl ether

Sources & evidence

ORD record
ord-5c9273bed51b4855af87ab9f64e53816
Source dataset
uspto-grants-1988_04
Patent number
US04740516

Reaction notes

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