1H-1,2,4-Triazole → Simeconazole

HRID 1464598Notes

Reaction equation

HRID 1464598 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.Cl[CH2:9][C:10]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)([OH:16])[CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13]>CN(C)C=O>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:10]([OH:16])([CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH2:9][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 12097219HCID 12097219, compound

Product 1

HCID 10085783SimeconazoleYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1.62 g (0.04 mole) of a 60% w/v dispersion of sodium hydride in mineral oil were added to 60 ml of dimethylformamide. Whilst the mixture was being stirred in an ice bath, 2.91 g (0.04 mole) of 1,2,4-triazole were added, and the mixture was stirred for a further 30 minutes at room temperature. At the end of this time, 5.5 g (0.021 mole) of 1 chloro-2-(4-fluorophenyl)-3-trimethylsilyl-2-propanol (prepared as described in Example 40) were added to the reaction mixture, which was then heated for 30 minutes at 90° C. whilst stirring. The reaction mixture was cooled and then poured into 200 ml of ice-water, and the resulting mixture was extracted with 300 ml of ethyl acetate. The organic extract was washed three times, each time with 100 ml of a saturated aqueous solution of sodium chloride. It was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure, to afford a crude oily product. 2.9 g (yield 47%) of the title compound, melting at 118 119° C., were obtained by purification of this crude oily product by silica gel column chromatography, using mixtures of ethyl acetate and hexane in proportions of 1:5, 1:1 and 2:1 as the eluent.

Workup

  1. stirringthe mixture was stirred for a further 30 minutes at room temperature
  2. stirringwhilst stirring
  3. temperatureThe reaction mixture was cooled
  4. extractionthe resulting mixture was extracted with 300 ml of ethyl acetate
  5. extractionThe organic extract
  6. washwas washed three times
  7. dry with materialIt was then dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. customto afford a crude oily product

Sources & evidence

ORD record
ord-6f928412aafa4c20ab727b661f4c50b8
Source dataset
uspto-grants-1994_04
Patent number
US05306712

Reaction notes

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