Potassium Carbonate → HCID 20035468, compound

HRID 1905406Notes

Reaction equation

HRID 1905406 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[N:12]([CH3:13])[N:11]=[C:10]([CH3:14])[C:9]=2[CH:15]=[N:16]O)=[CH:5][CH:4]=1.[C:20]([NH:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([CH2:32]Cl)=[CH:28][CH:27]=1)([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:20]([NH:24][C:25](=[O:34])[C:26]1[CH:27]=[CH:28][C:29]([CH2:32][N:16]=[CH:15][C:9]2[C:10]([CH3:14])=[N:11][N:12]([CH3:13])[C:8]=2[O:7][C:6]2[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:30][CH:31]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20035464HCID 20035464, compoundHCID 73189345HCID 73189345, compound

Product 1

HCID 20035468HCID 20035468, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1.0 Gram (0.0038 mole) of 5-(4-methoxyphenoxy)-1,3-dimethylpyrazole-4-carbaldehyde oxime, 0.86 g (0.0038 mole) of N-tert-butyl-4-chloromethylbenzamide and 1.0 g (0.0072 mole) of potassium carbonate were added to 20 ml of acetonitrile, and the resulting mixture was heated under reflux for 6 hours. After completion of the reaction, acetonitrile was removed by evaporation under reduced pressure, after which water was added to the residue and extraction was carried out with ethyl acetate. The ethyl acetate extract was washed with water and dried, and ethyl acetate was removed by evaporation to obtain an oily product. This oily product was column-chromatographed on silica gel to obtain 1.4 g of the desired compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customwas removed by evaporation under reduced pressure
  4. additionafter which water was added to the residue and extraction
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. customdried
  8. customethyl acetate was removed by evaporation
  9. customto obtain an oily product
  10. customThis oily product was column-chromatographed on silica gel

Sources & evidence

ORD record
ord-ef59a0fbcae94144a9a6bafd51101a9d
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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