Hydrochloric Acid → N-Benzoyl-3-(2-furoyl)-2-oxindole-1-carboxamide

HRID 542589Notes

Reaction equation

HRID 542589 reaction equation
[C:1]([NH:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:21])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](Cl)=[O:28].O.Cl>CN(C1C=CN=CC=1)C.CN(C)C=O>[C:1]([NH:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]([C:27]([C:23]2[O:22][CH:26]=[CH:25][CH:24]=2)=[O:28])[C:13]1=[O:21])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 682422-Furancarbonyl chlorideHCID 13910502HCID 13910502, compound

Product 1

HCID 13910498N-Benzoyl-3-(2-furoyl)-2-oxindole-1-carboxamideYield 78.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To 30 ml of N,N-dimethylformamide was added, with stirring, 2.8 g (10 mmole) of N-benzoyl-2-oxindole-1-carboxamide, followed by 2.9 g (24 mmole) of 4-(N,N-dimethylamino)pyridine. The mixture was cooled in an ice-bath and then to it was added, dropwise, with stirring, during 10 minutes, a solution of 1.6 g (12 mmole) of 2-furoyl chloride in 10 ml of N,N-dimethylformamide. Stirring was continued for 30 minutes and then the reaction mixture was poured into a mixture prepared from 250 ml of water and 8.5 ml of 3N hydrochloric acid. The resulting mixture was cooled in an ice-bath and the solid was removed by filtration. The solid was recrystallized from ca. 75 ml of acetic acid to give 2.94 g of the title compound as yellow-brown crystals, mp 190° C.

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. additionto it was added
  3. stirringdropwise, with stirring, during 10 minutes
  4. stirringStirring
  5. additionthe reaction mixture was poured into a mixture
  6. temperatureThe resulting mixture was cooled in an ice-bath
  7. customthe solid was removed by filtration
  8. customThe solid was recrystallized from ca. 75 ml of acetic acid

Sources & evidence

ORD record
ord-1d2b78f7946a46e7af6be1469be8a08a
Source dataset
uspto-grants-1987_04
Patent number
US04658037

Reaction notes

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