1H-1,2,4-Triazole → Simeconazole

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

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.