4-Chlorobenzaldehyde → HCID 54122748, compound

HRID 579767Notes

Reaction equation

HRID 579767 reaction equation
[CH3:1][C:2]1([C:5](=[O:12])[CH2:6][N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)[CH2:4][CH2:3]1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(OC(=O)C)(=O)C>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[C:6]([N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)[C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)=[O:12])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 11430Potassium CarbonateHCID 12760574HCID 12760574, compound

Product 1

HCID 54122748HCID 54122748, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

1-(1-Methylcyclopropyl)-2-(1,2,4-triazole-1-yl)ethane-1-one (10 g, 0.06 mole), 4-chlorobenzaldehyde (9 g, 0.06 mole), anhydrous potassium carbonate (8 g, 0.06 mole) and acetic anhydride (100 ml) were mixed, and the mixture was heated to 100° C. for 6 hours with stirring. Precipitates in the reaction solution was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain an oily product. The oily product was extracted with chloroform (300 ml), and the extract was washed with a sodium hydrogen carbonate-saturated water (300 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. One drop of the residue was dissolved in acetone, and the acetone solution was gas-chromatographed under the conditions described below. Then, a peak corresponding to the II-A isomer was found at a retention time of 250 sec, and that corresponding to the II-B isomer at a retention time of 300 sec. The ratio of the both isomers was 19.1/63.5, i.e. about 1/3, as calculated from the percentage of each area.

Workup

  1. customPrecipitates in the reaction solution
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto obtain an oily product
  5. extractionThe oily product was extracted with chloroform (300 ml)
  6. washthe extract was washed with a sodium hydrogen carbonate-saturated water (300 ml)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionOne drop of the residue was dissolved in acetone
  10. customthe acetone solution was gas-chromatographed under the conditions

Sources & evidence

ORD record
ord-2c77f08a9ea64c02a82f3b172fce27c6
Source dataset
uspto-grants-1988_06
Patent number
US04749716

Reaction notes

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