1H-1,2,4-Triazole → Simeconazole

HRID 1464599Notes

Reaction equation

HRID 1464599 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH2:17][O:16]2)=[CH:11][CH:10]=1>CC(N(C)C)=O>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([OH:16])([CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH2:17][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 19086784HCID 19086784, compound

Product 1

HCID 10085783SimeconazoleYield 55.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.237 g (6.18 mmole) of a 60% w/v dispersion of sodium hydride in mineral oil was added to 10 ml of dimethylacetamide. The mixture was then cooled in an ice-water bath, after which 0.854 g (12.37 mmole) of 1,2,4-triazole was added, whilst stirring. The reaction mixture was stirred for 30 minutes, and then 1.4 g (6.24 mmole) of 2-(4-fluorophenyl)-2-trimethylsilylmethyloxirane (prepared as described in Example 66) were added. The mixture was stirred for a further 2 hours at 80° C., after which it was cooled, and the mixture was poured into 50 ml of ice water and extracted with 100 ml of ethyl acetate. The organic extract was washed twice, each time with 50 ml of a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to obtain crude crystals These crystals were recrystallized from diisopropyl ether, to give 1.01 g (yield 55%) of the title compound, as crystals, melting at 118°-119° C.

Workup

  1. temperatureThe mixture was then cooled in an ice-water bath
  2. stirringThe reaction mixture was stirred for 30 minutes
  3. stirringThe mixture was stirred for a further 2 hours at 80° C.
  4. temperatureafter which it was cooled
  5. extractionextracted with 100 ml of ethyl acetate
  6. extractionThe organic extract
  7. washwas washed twice
  8. dry with materialeach time with 50 ml of a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  9. customThe solvent was then removed by distillation under reduced pressure
  10. customto obtain crude crystals These crystals
  11. customwere recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e63c4b7c1ec044c79704cf13be7d985a
Source dataset
uspto-grants-1994_04
Patent number
US05306712

Reaction notes

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