Water → 5-{4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-alpha-fluorobenzyl}-3-(2-chloro-6-fluorophenyl)-1 methyl-1H-1,2,4-triazole

HRID 443043Notes

Reaction equation

HRID 443043 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:34]=[CH:33][C:16]([CH:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[Cl:32])[N:20]=3)O)=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(N(S(F)(F)[F:41])CC)C.O>C1C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:34]=[CH:33][C:16]([CH:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[Cl:32])[N:20]=3)[F:41])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 53993399HCID 53993399, compound

Product 1

HCID 540753285-{4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-alpha-fluorobenzyl}-3-(2-chloro-6-fluorophenyl)-1 methyl-1H-1,2,4-triazoleYield 88.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 0.9 g of 5-{4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-α-hydroxybenzyl}-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole in 10 ml of benzene at room temperature, were added 0.85 g of diethylaminosulfur trifluoride (DAST). After stirring at room temperature for 1 hour, the reaction mixture was poured into iced water and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium hydrogen carbonate and then with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to afford 0.8 g of 5-{4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-α-fluorobenzyl}-3-(2-chloro-6-fluorophenyl)-1 methyl-1H-1,2,4-triazole.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated aqueous sodium hydrogen carbonate
  3. dry with materialwith water, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d022a2470554677b551218612a851a5
Source dataset
uspto-grants-1999_04
Patent number
US05892048

Reaction notes

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