Dimethylformamide → HCID 86748268, compound

HRID 2380271Notes

Reaction equation

HRID 2380271 reaction equation
CN(C)C=O.[CH:6]([O:9][N:10]=[C:11]([N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14](O)[CH:13]=1)([CH3:8])[CH3:7].[CH2:24](Br)[CH:25]([CH3:27])[CH3:26].[C:29](=O)([O-])[O-].[K+].[K+]>O>[CH:6]([O:9][N:10]=[C:11]([N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:29][CH2:24][CH:25]([CH3:27])[CH3:26])[CH:13]=1)([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 85664898HCID 85664898, compound

Product 1

HCID 86748268HCID 86748268, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 100 ml of N,N-dimethylformamide was added 1.2 g (4.9 mmol) of 1-(O-isopropyl-3-hydroxybenzohydroximoyl)-1H-1,2,4-triazole, 0.7 g (5.1 mmol) of isobutyl bromide, and 0.8 g (5.8 mmol) of potassium carbonate. The mixture was stirred for 1 hour at 80° C. to complete the reaction. The reaction mixture was allowed to sit and cool naturally. The cooled reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent in the organic layer was then removed under reduced pressure. The residue was purified by column chromatography, thus obtaining 1.1 g (yield: 73%) of the desired produce having a refractive index of [nD20 ] 1.5341 at 20° C.

Workup

  1. customthe reaction
  2. temperaturecool naturally
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent in the organic layer was then removed under reduced pressure
  7. customThe residue was purified by column chromatography
  8. customthus obtaining 1.1 g (yield: 73%) of the
  9. customdesired produce
  10. customat 20° C.

Sources & evidence

ORD record
ord-682c429fd6bb4db18f3fa65490348eff
Source dataset
uspto-grants-1994_11
Patent number
US05366988

Reaction notes

Loading…