Potassium Carbonate → HCID 44274391, compound

HRID 1283815Notes

Reaction equation

HRID 1283815 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:26]([O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])=[O:27]>O1CCOCC1>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:10]=2)=[CH:3][C:2]=1[NH:1][C:26](=[O:27])[O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 21390701HCID 21390701, compound

Product 1

HCID 44274391HCID 44274391, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 5-(3-amino-4-chlorophenyl)-3-(2-furanyl)-1,2,4-oxadiazole (0.75 g) and 0.58 g of potassium carbonate in 25 ml of dioxane is added 0.80 g of 2,2,2-trichloroethyl chloroformate. The resulting mixture is heated at reflux for 2 hours, and concentrated to dryness. 50 ml of water is added to the residue and the resulting mixture is extracted three times with chloroform. The extracts are dried over magnesium sulfate, filtered and concentrated to dryness. The residue is absorbed on an alumina column and eluted with benzene to give 0.50 g of the title compound, melting point 114°-116°C.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated to dryness
  4. addition50 ml of water is added to the residue
  5. extractionthe resulting mixture is extracted three times with chloroform
  6. dry with materialThe extracts are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue is absorbed on an alumina column
  10. washeluted with benzene

Sources & evidence

ORD record
ord-1d6f65865f0a4f0f9c6e361c6a24b0f8
Source dataset
uspto-grants-1976_08
Patent number
US03976657

Reaction notes

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