Dimethylformamide → 3-(2-chloro-6-fluorophenyl)-5-[3-chloro-4-(4-trifluoromethylphenoxymethyl)phenyl]-1-methyl-1H-1,2,4-triazole

HRID 52220

Reaction equation

HRID 52220 reaction equation
CN(C)C=O.[F:6][C:7]([F:16])([F:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:35]([CH3:36])[N:34]=[C:33]([C:37]3[C:42]([F:43])=[CH:41][CH:40]=[CH:39][C:38]=3[Cl:44])[N:32]=2)=[CH:27][C:26]=1[Cl:45]>O>[Cl:44][C:38]1[CH:39]=[CH:40][CH:41]=[C:42]([F:43])[C:37]=1[C:33]1[N:32]=[C:31]([C:28]2[CH:29]=[CH:30][C:25]([CH2:24][O:14][C:11]3[CH:10]=[CH:9][C:8]([C:7]([F:15])([F:16])[F:6])=[CH:13][CH:12]=3)=[C:26]([Cl:45])[CH:27]=2)[N:35]([CH3:36])[N:34]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 214636485-(4-bromomethyl-3-chlorophenyl) 3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole

Product 1

HCID 214635883-(2-chloro-6-fluorophenyl)-5-[3-chloro-4-(4-trifluoromethylphenoxymethyl)phenyl]-1-methyl-1H-1,2,4-triazoleYield 78.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of N,N-dimethylformamide are added 4-trifluoromethyl phenol (0.77 g) and potassium carbonate (0.72 g) and 5-(4-bromomethyl-3-chlorophenyl)-3(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole (1.60 g) is added thereto at room temperature with stirring, which is stirred at 120° C. for 1 hour. On completion of the reaction, the reaction solution is cooled to room temperature, poured into water and extracted with toluene. 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 1.50 g of desired compound (refractive index: 1.5961).

Workup

  1. additionis added
  2. stirringwhich is stirred at 120° C. for 1 hour
  3. customOn completion of the reaction
  4. temperaturethe reaction solution is cooled to room temperature
  5. extractionextracted with toluene
  6. washThe organic layer is washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fa4a457f5b2f4341835865c0b6b34cb6
Source dataset
uspto-grants-1997_04
Patent number
US05616594

Linked notes

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