Dimethylformamide → HCID 178439190, compound

HRID 1779983Notes

Reaction equation

HRID 1779983 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([CH3:21])=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:11][O:10]1.[NH:22]1[CH:26]=NC=[N:23]1.CC(C)([O-])C.[K+].[CH3:33][N:34](C)C=O>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:12]([CH3:21])=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)([OH:10])[CH2:11][C:33]1[N:34]=[N:23][NH:22][CH:26]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 23665647Potassium tert-butoxideHCID 54127016HCID 54127016, compound

Product 1

HCID 178439190HCID 178439190, compoundYield 36%

Conditions

Temperature
100 °C

Procedure

To 40 ml of N,N-dimethylformamide Were dissolved 2.0 g of 2-(2,4-difluorophenyl)-2-[1-methyl-2-(4-fluorophenyl)-ethenyl]-oxirane, 1.9 g of 1,2,4-triazole and 1.6 g of potassium t-butoxide. After 4 hours of stirring at 100° C., the reaction solution was cooled to room temperature, poured into ice water and then extracted with ethyl acetate. The resulting organic layer was washed with water and dried on anhydrous magnesium sulfate. After removing the solvent by evaporation under a reduced pressure, the resulting residue was purified by a silica gel column chromatography (ethyl acetate) to obtain 1.6 g of 2-(2,4-difluorophenyl)-2-[1-methyl-2-(4-fluorophenyl)-ethenyl]-1-triazolyl-2-ethanol with a yield of 36%.

Workup

  1. temperaturethe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic layer was washed with water
  4. dry with materialdried on anhydrous magnesium sulfate
  5. customAfter removing the solvent
  6. customby evaporation under a reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-bf6abaec4bea4e86a478cc7acf270deb
Source dataset
uspto-grants-1997_05
Patent number
US05629332

Reaction notes

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