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1H-1,2,4-Triazole → HCID 12765983, compound

HRID 1995925
Notes
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Reaction equation

HRID 1995925 reaction equation
BrBr.[Cl:3][C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][C:10](=[O:23])[C:11]([CH3:22])([CH3:21])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:6][CH:5]=1.[NH:26]1[CH:30]=[N:29][CH:28]=[N:27]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)(Cl)Cl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([N:26]2[CH:30]=[N:29][CH:28]=[N:27]2)[C:10](=[O:23])[C:11]([CH3:21])([CH3:22])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 24408BromineHCID 127659751-(4-Chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-butan-2-one

Product 1

HCID 12765983HCID 12765983, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 5943
Carbon Tetrachloride
Solvent

Procedure

48 g (0.3 mol) of bromine were added dropwise to 110.5 g (0.3 mol) of 1-(4-chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-butan-2-one in 750 ml of carbon tetrachloride at room temperature. The mixture was subsequently stirred at room temperature for one hour and was concentrated by distilling off the solvent in vacuo, and the residue was taken up in 750 ml of toluene. 73 g (1.06 mol) of 1,2,4-triazole and 150 g (1.06 mol) of potassium carbonate were added to this solution. The mixture was heated to 90° C. for 8 hours and allowed to cool to room temperature and the organic phase was separated off. This phase was extracted with dilute sodium hydroxide solution, rinsed with water, dried over sodium sulphate and concentrated in vacuo. 34 g (26% of theory) of 1-(4-chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of melting point 115° C. were obtained.

Workup

  1. concentrationwas concentrated
  2. distillationby distilling off the solvent in vacuo
  3. temperatureThe mixture was heated to 90° C. for 8 hours
  4. temperatureto cool to room temperature
  5. customthe organic phase was separated off
  6. extractionThis phase was extracted with dilute sodium hydroxide solution
  7. washrinsed with water
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b03004be0eab43d6b40fb7c566bc40e4
Source dataset
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04406909

Reaction notes

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