1H-1,2,4-Triazole → HCID 54231880, compound

HRID 1065784Notes

Reaction equation

HRID 1065784 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH3:19])([CH3:18])[C:6](=[O:17])[CH:7](Br)[O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[CH3:2].[NH:21]1[CH:25]=[N:24][CH:23]=[N:22]1>C(#N)C>[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH3:19])([CH3:18])[C:6](=[O:17])[CH:7]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)[CH3:2]

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 53994102HCID 53994102, compound

Product 1

HCID 54231880HCID 54231880, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

34 g (0.091 mol) of 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-keto-butanoic acid ethyl ester were dissolved in 240 ml of acetonitrile. 24 g (0.345 mol) of 1,2,4-triazole were added and the mixture was heated for 48 hours under reflux. The solvent was then distilled off in vacuo, the residue was dissolved in 200 ml of methylene chloride and the solution was washed three times with 50 ml of water each time, dried over sodium sulphate and concentrated. The oil which remained was boiled up with 100 ml of petroleum ether, whereupon it crystallized. The solid was filtered off and dried. 24.9 g (78% of theory) of 4-(4-chlorophenoxy)-2,2-dimethyl-3-keto-4-(1,2,4-triazol-1-yl)-butanoic acid ethyl ester of melting point 88°-89° C. were obtained.

Workup

  1. temperaturethe mixture was heated for 48 hours
  2. temperatureunder reflux
  3. distillationThe solvent was then distilled off in vacuo
  4. dissolutionthe residue was dissolved in 200 ml of methylene chloride
  5. washthe solution was washed three times with 50 ml of water each time
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customcrystallized
  9. filtrationThe solid was filtered off
  10. customdried

Sources & evidence

ORD record
ord-9d89c8bd42524437843c9e76de4b43aa
Source dataset
uspto-grants-1982_05
Patent number
US04331674

Reaction notes

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