Dimethylformamide → HCID 86748268, compound

HRID 2380270Notes

Reaction equation

HRID 2380270 reaction equation
CN(C)C=O.[CH:6]([O:9][N:10]=[C:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH:13]=1)([CH3:8])[CH3:7].[NH:24]1[CH:28]=[N:27][CH:26]=[N:25]1.C(=O)([O-])[O-].[K+].[K+]>O>[CH:6]([O:9][N:10]=[C:11]([N:24]1[CH:28]=[N:27][CH:26]=[N:25]1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH:13]=1)([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 85664896HCID 85664896, compound

Product 1

HCID 86748268HCID 86748268, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To 100 ml of N,N-dimethylformamide was added 1.5 g (5.6 mmol) of O-isopropyl-3-isopentylbenzohydroximoyl chloride, 0.8 g (11.6 mmol) of 1,2,4-triazole, and 1.6 g (11.6 mmol) of potassium carbonate. The mixture was stirred at 120° C. for 3 hours to complete the reaction. The reaction mixture was allowed to sit and cool naturally to room temperature. The cooled reaction mixture was poured into water and extracted with ethyl acetate. After being washed with water, 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 1.2 g (yield: 71%) of the desired product having a refractive index of [nD20 ] 1.5317 at 20° C.

Workup

  1. customthe reaction
  2. temperaturecool naturally to room temperature
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate
  5. washAfter being washed with water
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent in the organic layer was then removed under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-08dcaa22fefc4de09b515280382fb81a
Source dataset
uspto-grants-1994_11
Patent number
US05366988

Reaction notes

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