1H-1,2,4-Triazole → HCID 19098835, compound

HRID 1975840Notes

Reaction equation

[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2([C:10]3([CH3:15])[CH2:12][C:11]3([F:14])[F:13])[CH2:9][O:8]2)=[CH:4][CH:3]=1.[NH:18]1[CH:22]=[N:21][CH:20]=[N:19]1>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]([C:10]2([CH3:15])[CH2:12][C:11]2([F:14])[F:13])([OH:8])[CH2:9][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 6.3 g (0.026 mol) of 2-(4-fluorobenzyl)-2-(2,2-difluoro-1-methyl-cyclopropyl)-oxirane in 5 ml of dimethylformamide is added dropwise with stirring at 80° C. to a mixture of 4.6 g (0.066 mol) of 1,2,4-triazole and 0.5 g (0.0045 mol) of potassium tert.-butylate in 10 ml of dimethylformamide. When the addition is complete, the reaction mixture is stirred for 8 hours at 80° C. The solvent is subsequently stripped off under reduced pressure and the residue which remains is dissolved in ethyl acetate. The organic solution is washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed on silica gel using dichloromethane as the eluent. After the eluate has been evaporated, 1.7 g (21% of theory) of 1-(4-fluorophenyl)-2-(2,2-difluoro-1-methyl-cyclopropyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol are obtained in the form of a solid substance of melting point 114° C.

Workup

additionWhen the addition
washThe organic solution is washed with water
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue is chromatographed on silica gel
customAfter the eluate has been evaporated

Sources & evidence

ORD record: ord-9a4941693400414e92b7bdcb6862e376
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05288883

Reaction notes

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