Dimethylformamide → HCID 21463625, compound

HRID 1940718Notes

Reaction equation

HRID 1940718 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:15]2[N:19]([CH3:20])[N:18]=[C:17]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])[N:16]=2)[CH:10]=[CH:11][C:12]=1[CH2:13]Cl.C(=O)([O-])[O-].[K+].[K+].[F:35][C:36]1[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:37]=1[OH:46]>O>[Cl:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([F:27])[C:21]=1[C:17]1[N:16]=[C:15]([C:9]2[CH:10]=[CH:11][C:12]([CH2:13][O:46][C:37]3[CH:38]=[CH:39][C:40]([C:42]([F:43])([F:44])[F:45])=[CH:41][C:36]=3[F:35])=[C:7]([Cl:6])[CH:8]=2)[N:19]([CH3:20])[N:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5226542-Fluoro-4-(trifluoromethyl)phenolHCID 21463590HCID 21463590, compound

Product 1

HCID 21463625HCID 21463625, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 ml of N,N-dimethylformamide are added 5-(3-chloro-4-chloromethylphenyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole (1.60 g) and potassium carbonate (0.60 g) and 2-fluoro-4-trifluoromethyl phenol (0.80 g) is added thereto at room temperature with stirring, which is stirred at 70° C. for 3 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 1.62 g of desired compound (refractive index: 1.6010).

Workup

  1. additionis added
  2. stirringwhich is stirred at 70° C. for 3 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-0b3bdadcf86e42a78dbefe8496eb9355
Source dataset
uspto-grants-1997_12
Patent number
US05700824

Reaction notes

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