Hydrochloric Acid → Tebuconazole

HRID 1651746Notes

Reaction equation

HRID 1651746 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:18][O:17]2)=[CH:10][CH:9]=1.[NH:23]1[CH:27]=[N:26][CH:25]=[N:24]1.Cl>O.CS(C)=O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([CH2:18][N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)([OH:17])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 92571H-1,2,4-TriazoleHCID 10340Sodium CarbonateHCID 946842-tert-Butyl-2-(2-(4-chlorophenyl)ethyl)oxirane

Product 1

HCID 86102TebuconazoleYield 42%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

5.3 g (0.05 mole) of sodium carbonate were added to a mixture of 245.2 g (1 mole) of 2-(4-chlorophenylethyl)-2-tert.-butyl-oxirane (97.2% pure), 72.5 g (1 mole) of 1,2,4-triazole (95.2% pure) and 380 ml of dimethylsulphoxide at room temperature, while stirring, and the mixture was then heated at 110° C. for 4 hours. Thereafter, the reaction mixture was poured into 1 liter of water and neutralized with dilute aqueous hydrochloric acid. The liquid phase was decanted off from the solid and the residue was dissolved in 1 liter of toluene. The solution was extracted with water, the phases were separated and the organic phase was dried and concentrated by stripping off the diluent under reduced pressure. 128 g (42% of theory) of 1-(4-chlorophenyl)-3-(1,2,4-triazol-1-ylmethyl)-4,4-dimethyl-pentan-3-ol were obtained in this manner in the form of a solid.

Workup

  1. customThe liquid phase was decanted off from the solid
  2. dissolutionthe residue was dissolved in 1 liter of toluene
  3. extractionThe solution was extracted with water
  4. customthe phases were separated
  5. customthe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0dfce1b532914836a49893d7a04ca283
Source dataset
uspto-grants-1990_05
Patent number
US04929735

Reaction notes

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