Potassium Carbonate → HCID 44274505, compound

HRID 1283819Notes

Reaction equation

HRID 1283819 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].C(=O)([O-])[O-].[K+].[K+].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:27][N:26]=[C:25]([C:28]3[O:29][CH:30]=[CH:31][CH:32]=3)[N:24]=2)=[C:19]([Cl:33])[CH:18]=1>O1CCOCC1>[Cl:33][C:19]1[CH:18]=[C:17]([NH:16][C:2](=[O:3])[O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])[CH:22]=[CH:21][C:20]=1[C:23]1[O:27][N:26]=[C:25]([C:28]2[O:29][CH:30]=[CH:31][CH:32]=2)[N:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 21516665HCID 21516665, compound

Product 1

HCID 44274505HCID 44274505, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,2,2-Trichloroethyl chloroformate (1.56 g) is added to a mixture of 1.05 g of potassium carbonate and 1.3 g of 5-(4-amino-2-chlorophenyl)-3-(2-furanyl)-1,2,4-oxadiazole in 30 ml of dioxane. The mixture is heated at reflux for 2 hours and concentrated to dryness. The residue is partitioned between water and chloroform and the aqueous layer is extracted twice with chloroform. The combined chloroform extract is dried, filtered and concentrated to yield the crude product. Recrystallization from benzene/dioxane yields 1.2 g of the title compound, melting point 219°-220°C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated to dryness
  4. customThe residue is partitioned between water and chloroform
  5. extractionthe aqueous layer is extracted twice with chloroform
  6. extractionThe combined chloroform extract
  7. customis dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield the crude product
  11. customRecrystallization from benzene/dioxane

Sources & evidence

ORD record
ord-a660688277d547a4b12f7b1fe1ec80d4
Source dataset
uspto-grants-1976_08
Patent number
US03976657

Reaction notes

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