1H-1,2,4-Triazole → HCID 19010587, compound

HRID 1741655Notes

Reaction equation

HRID 1741655 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][C:5]1([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)[CH2:7][O:6]1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1>CN(C)C=O>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][C:5]([C:8]1([C:11]#[N:12])[CH2:10][CH2:9]1)([OH:6])[CH2:7][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 19010586HCID 19010586, compound

Product 1

HCID 19010587HCID 19010587, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.26 g (10.4mmol) of 2-(2-fluorobenzyl)-2-(1-cyanocyclo-propyl)-oxirane in 10 ml of dimethylformamide are added dropwise at 80° C. with stirring to a solution of 0.23 g (2.1 mmol) of potassium tert.-butylate and 2.15 g (31.2 mmol) of 1,2,4-triazole in 10 ml of dimethylformamide. When the addition has ended, stirring of the reaction mixture is continued for 4 hours at 80° C. The mixture is subsequently concentrated under reduced pressure, and the residue is taken up in ethyl acetate/water. The aqueous phase is extracted three times using ethyl acetate. The combined organic extracts are dried over sodium sulphate, concentrated under reduced pressure and chromatographed on silica gel using the eluent cyclohexane/ethyl acetate =1:1. 1.37 g (46% of theory) of 1-(2-fluorophenyl)-2-(1-cyanocyclopropyl)-3-(1,2,4-triazol-1-yl)-propan -2-ol are isolated.

Workup

  1. additionWhen the addition
  2. concentrationThe mixture is subsequently concentrated under reduced pressure
  3. extractionThe aqueous phase is extracted three times
  4. dry with materialThe combined organic extracts are dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on silica gel using the eluent cyclohexane/ethyl acetate =1:1

Sources & evidence

ORD record
ord-3d54b706cdb248b9b7ce68883f0e18f4
Source dataset
uspto-grants-1994_08
Patent number
US05334608

Reaction notes

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