Potassium Carbonate → HCID 15228844, compound

HRID 1708142Notes

Reaction equation

HRID 1708142 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14](=[N:16][OH:17])[NH2:15])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:20](Cl)(=O)[CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]3[N:15]=[C:20]([CH2:21][CH3:22])[O:17][N:16]=3)=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62324Propionyl chlorideHCID 53844460HCID 53844460, compound

Product 1

HCID 15228844HCID 15228844, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

There was suspended, in 5 ml of dry pyridine, 521 mg of 4-[3-(1H-imidazol-1-yl)propoxy]benzamidoxime. After gradual and dropwise addition of 194 mg of propionyl chloride and stirring at room temperature for one hour, the suspension was heated to a temperature ranging from 80° to 90° C. for 3.5 hours with stirring. The suspension was added to ice water and the pH thereof was adjusted to 9 to 10 by the addition of potassium carbonate. Then the suspension was extracted with ether and the extract was washed with water and then dried. After concentration of the extract, the resulting residue was purified by silica gel column chromatography (eluent: 98% chloroform-ethanol). n-Hexane was added to the resulting fraction to crystallize the product, followed by filtration to give 431 mg (yield 72.2%) of 3-[4 -[3-(1H-imidazol-1-yl)propoxy]phenyl]-5-ethyl-1,2,4-oxadiazole having a melting point of 74.0°-75.5 ° C.

Workup

  1. temperaturethe suspension was heated to a temperature
  2. waitranging from 80° to 90° C. for 3.5 hours
  3. stirringwith stirring
  4. extractionThen the suspension was extracted with ether
  5. washthe extract was washed with water
  6. customdried
  7. customAfter concentration of the extract, the resulting residue was purified by silica gel column chromatography (eluent: 98% chloroform-ethanol)
  8. additionn-Hexane was added to the resulting fraction
  9. customto crystallize the product
  10. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-6c4d7dada55342f4b1a7a68556aa6b54
Source dataset
uspto-grants-1994_10
Patent number
US05356916

Reaction notes

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