Water → HCID 53694765, compound

HRID 443038Notes

Reaction equation

HRID 443038 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[N:8]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:30]1[C:35]([Cl:36])=[CH:34][C:33]([C:37]([F:40])([F:39])[F:38])=[CH:32][N:31]=1.O>CN(C=O)C>[Cl:36][C:35]1[C:30]([O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][C:7]3[N:11]([CH3:12])[N:10]=[C:9]([C:13]4[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=4[F:20])[N:8]=3)=[CH:21][CH:22]=2)=[N:31][CH:32]=[C:33]([C:37]([F:39])([F:38])[F:40])[CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 54206388HCID 54206388, compound

Product 1

HCID 53694765HCID 53694765, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.8 g of 5-(4-hydroxybenzyl)-3-(2,6-difluorophenyl)-1-methyl 1H-1,2,4-triazole in 10 ml of DMF at room temperature were added 0.4 g of anhydrous potassium carbonate and 0.63 g of 2,3-dichioro-5-trifluoromethylpyridine and then the suspension solution was heated to 70° C. or 1 hour. After cooling, the reaction mixture was poured into iced water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to afford 0.55 g of 5-(4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-benzyl)-3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazole.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a56f157541f42c4a63c73269f8ea336
Source dataset
uspto-grants-1999_04
Patent number
US05892048

Reaction notes

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