1H-1,2,4-Triazole → HCID 14348465, compound

HRID 1031327Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]2([S:15][C:16]([F:19])([F:18])[F:17])[CH2:14][CH2:13]2)[CH2:11][O:10]1.[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([C:12]1([S:15][C:16]([F:19])([F:18])[F:17])[CH2:14][CH2:13]1)[CH2:11][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 15.9 g (54 mmol) of 2-(2,4-difluoro- phenyl)-2-[1-(trifluoromethylmercapto)-cycloprop-1-yl]oxirane in 20 ml of absolute dimethylformamide is added dropwise with stirring to a mixture of 12 g (174 mmol) of 1,2,4-triazole and 1.4 g (12.5 mmol) of potassium tert.butylate in 30 ml of absolute dimethylformamide under a nitrogen atmosphere The reaction mixture is stirred at 100° C. for 8 hours. The solvent is then stripped off under reduced pressure, the residue is taken up in ethyl acetate, and the solution is washed twice with water and concentrated under reduced pressure after drying over sodium sulphate The residue is chromatographed on a silica gel column using chloroform as eluent. In this manner, 12.5 g (65 % of theory) of 1-(2,4-difluorophenyl)-1-hydroxy-2-(1,2,4-triazol-1-yl)-1-(1-trifluoromethylmercapto-cycloprop-1-yl)ethane of melting point 103° C. are obtained.

Workup

washthe solution is washed twice with water
concentrationconcentrated under reduced pressure
dry with materialafter drying over sodium sulphate The residue
customis chromatographed on a silica gel column

Sources & evidence

ORD record: ord-87fb40700fdb410ea550a5d81056dad4
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04954162

Reaction notes

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