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

HRID 1731313Notes

Reaction equation

HRID 1731313 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 mol) of 1,2,4-triazole and 13.8 g (0.1 mol) of potassium carbonate in 200 ml of acetone. The reaction mixture is stirred under reflux for 20 hours. Thereafter, the mixture is 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). The column is first eluted with chloroform. 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. filtrationThereafter, the mixture is 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. washThe column is first eluted with chloroform
  10. customThe eluate thereby obtained
  11. concentrationis concentrated
  12. distillationby distilling off the solvent
  13. stirringthe residue is stirred with diethyl ether

Sources & evidence

ORD record
ord-b02b70a966454fcb8f8bc0a4cfcdae55
Source dataset
uspto-grants-1986_11
Patent number
US04621095

Reaction notes

Loading…