2-Furancarbonyl chloride → HCID 13565652, compound

HRID 1382802Notes

Reaction equation

HRID 1382802 reaction equation
[Na].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](Cl)=[O:18]>C(O)C>[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:2][C:3]1=[O:11])=[O:18]

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 321710OxindoleHCID 5360545Sodium

Product 1

HCID 13565652HCID 13565652, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5.5 g (0.24 mole) of sodium in 150 ml of ethanol was added 13.3 g (0.10 mole) of 2-oxindole at room temperature. The resulting slurry was cooled to ice-bath temperature, and then 15.7 g (0.12 mole) of 2-furoyl chloride was added, dropwise, during 10-15 minutes. The ice-bath was removed, and an additional 100 ml of ethanol was added and then the reaction mixture was heated under reflux for 7 hours. The reaction mixture was allowed to stand overnight and then the solid was filtered off. The solid was added to 400 ml of water and the resulting mixture was acidified using concentrated hydrochloric acid. The mixture was cooled with ice and the solid was collected by filtration. The solid residue was recrystallized from 150 ml of acetic acid, affording 8.3 g of yellow crystals, m.p. 209°-210° C. (dec.). Analysis: Calcd. for C13H9O3N: C, 68.72; H, 3.99; N, 6.17%. Found: C, 68.25; H, 4.05; N, 6.20%.

Workup

  1. temperatureThe resulting slurry was cooled to ice-bath temperature
  2. customThe ice-bath was removed
  3. additionan additional 100 ml of ethanol was added
  4. temperaturethe reaction mixture was heated
  5. temperatureunder reflux for 7 hours
  6. waitto stand overnight
  7. filtrationthe solid was filtered off
  8. additionThe solid was added to 400 ml of water
  9. temperatureThe mixture was cooled with ice
  10. filtrationthe solid was collected by filtration
  11. customThe solid residue was recrystallized from 150 ml of acetic acid

Sources & evidence

ORD record
ord-81907074c68d423f9944c111a4d27405
Source dataset
uspto-grants-1989_02
Patent number
US04808601

Reaction notes

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