Water → 3-(2-chloro-6-fluorophenyl)-5-[2-chloro-4-(3-chloro-5-trifluoromethylpyridine-2-yloxymethyl)phenyl]-1-methyl-1H-1,2,4-triazole

HRID 52225

Reaction equation

HRID 52225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:15]=2[Cl:22])[N:11]([CH3:23])[N:10]=1.[H-].[Na+].Cl[C:27]1[C:32]([Cl:33])=[CH:31][C:30]([C:34]([F:37])([F:36])[F:35])=[CH:29][N:28]=1.O>COCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:27]3[C:32]([Cl:33])=[CH:31][C:30]([C:34]([F:37])([F:35])[F:36])=[CH:29][N:28]=3)=[CH:16][C:15]=2[Cl:22])[N:11]([CH3:23])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 214636183-(2-chloro-6-fluorophenyl)-5-(2-chloro-4-hydroxymethylphenyl) 1-methyl-1H-1,2,4-triazole

Product 1

HCID 214636803-(2-chloro-6-fluorophenyl)-5-[2-chloro-4-(3-chloro-5-trifluoromethylpyridine-2-yloxymethyl)phenyl]-1-methyl-1H-1,2,4-triazoleYield 82.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(2-chloro-6-fluorophenyl)-5-(2-chloro-4-hydroxymethylphenyl) 1-methyl-1H-1,2,4-triazole (0.50 g) is dissolved in 1,2-dimethoxyethane (20 ml) and cooled to 0° C., to which is added sodium hydride (60%, 0.07 g) and the reaction mixture is stirred for 15 minutes. Then, a solution of 2,3-dichloro-5-trifluoromethyl pyridine (0.34 g) in 1,2-dimethoxyethane (10 ml) is added dropwise and stirred for 3 hours. On completion of the reaction, the reaction solution is warmed to room temperature and poured into water and extracted with ether. The organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography to give 0.62 g of desired compound.

Workup

  1. stirringstirred for 3 hours
  2. customOn completion of the reaction
  3. temperaturethe reaction solution is warmed to room temperature
  4. extractionextracted with ether
  5. washThe organic layer is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a27c64c90b344b65971f5c1a125fed1a
Source dataset
uspto-grants-1997_04
Patent number
US05616594

Linked notes

Loading…