1H-1,2,4-Triazole → HCID 14348382, compound

HRID 2072595Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

65 g (0.94 mol) of 1,2,4-triazole and 71 g (0.63 mol) of potassium tert.-butylate are taken in 160 ml of absolute dimethylformamide under a nitrogen atmosphere and are heated to 80° C. A solution of 70.6 g (0.26 mol) of 1-chloro-2-(1-chlorocyclopropyl)-3-(4-fluorophenyl)-propan-2-ol in 90 ml of absolute dimethylformamide is added dropwise at this temperature, with stirring. The mixture is subsequently stirred at 100° C. for 6 hours and is then concentrated by stripping off the diluent under reduced pressure. The residue is taken up in ethyl acetate, the mixture is washed with water and, after drying over sodium sulphate, the solvent is stripped off under reduced pressure. The product which remains is chromatographed over a silica gel column with chloroform as the mobile phase. 28.2 g (39% of theory) of 1-(4-fluorophenyl)-2-(1-chloro-cyclopropyl)-3-(1,2,4-triazol-1-yl)-propan -2-ol are obtained in this manner in the form of a solid substance of melting point 111° C.

Workup

stirringThe mixture is subsequently stirred at 100° C. for 6 hours
concentrationis then concentrated
washthe mixture is washed with water
dry with materialafter drying over sodium sulphate
customThe product which remains is chromatographed over a silica gel column with chloroform as the mobile phase

Sources & evidence

ORD record: ord-6e682dfb887743c29c9b0a2472f7a522
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04913727

Reaction notes

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