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

HRID 1940722Notes

Reaction equation

HRID 1940722 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([Cl:26])[CH:20]=2)[N:16]([CH3:27])[N:15]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:34][C:35]1[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[CH:39][C:36]=1[CH2:37]Cl>O>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:37][C:36]3[CH:39]=[CH:40][C:41]([C:43]([F:44])([F:46])[F:45])=[CH:42][C:35]=3[Cl:34])=[C:21]([Cl:26])[CH:20]=2)[N:16]([CH3:27])[N:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 214636572-Chloro-1-(chloromethyl)-4-(trifluoromethyl)benzeneHCID 136048655HCID 136048655, compound

Product 1

HCID 214636763-(2-chloro-6-fluorophenyl)-5-[3-chloro-4-(2-chloro-4-trifluoromethylbenzyloxy)phenyl]-1-methyl-1H-1,2,4-triazoleYield 72.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20 ml of N,N-dimethylformamide are added 3-(2-chloro-6-fluorophenyl)-5-(3-chloro-4-hydroxyphenyl)-1-methyl-1H-1,2,4-triazole (0.70 g) and potassium carbonate (0.31 g) and 2-chloro-4-trifluoromethylbenzyl chloride (0.50 g) is added thereto at room temperature with stirring, which is stirred at 120° C. for 5 hours. On completion of the reaction, the reaction solution is cooled to room temperature, poured into water and extracted with ethyl acetate. 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 0.80 g of desired compound (melting point: 156.0°-159.0° C.).

Workup

  1. additionis added
  2. stirringwhich is stirred at 120° C. for 5 hours
  3. customOn completion of the reaction
  4. temperaturethe reaction solution is cooled to room temperature
  5. extractionextracted with ethyl acetate
  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-c598666fa7324a0bae76fe680e584763
Source dataset
uspto-grants-1997_12
Patent number
US05700824

Reaction notes

Loading…