Dimethylformamide → HCID 13958007, compound

HRID 1382797Notes

Reaction equation

HRID 1382797 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:18])=[O:8].CN(C)C=O.[C:24](OC(=O)C)(=[O:26])[CH3:25]>CN(C1C=CN=CC=1)C.C1C=CC=CC=1>[C:24]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]([C:7](=[O:8])[CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C:10]1=[O:18])(=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 13565653HCID 13565653, compound

Product 1

HCID 13958007HCID 13958007, compoundYield 4.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent

Procedure

A stirred mixture of 1.29 g (5.0 mmole) of 3-([2-thienyl]acetyl)-2-oxindole, 1.22 g (10.0 mmole) of 4-(N,N-dimethylamino)pyridine and 15 ml of N,N-dimethylformamide was cooled in an ice-bath, and then 562 mg (5.5 mmole) of acetic anhydride was added dropwise, with stirring, during 1 minute. Stirring was continued for 3.25 hours at ice-bath temperature, and then the reaction mixture was filtered. The filtrate was poured onto a mixture of 3N hydrochloric acid and water, which caused formation of a solid and a gum. The solid was recovered by filtration and the gum was recovered by decantation. The gum was triturated under isopropanol-water giving further solid material, which was also recovered by filtration. The two solids were combined and extracted with hot benzene, leaving a dark, gummy residue. The benzene solution was cooled and evaporated in vacuo, and the residue was recrystallized from toluene to give 66 mg of the title compound, m.p. 136°-137° C. The mother liquors from the recrystallization were evaporated in vacuo and the latter residue was recrystallized from hexane to give a second crop, 90 mg, of the title compound, m.p. 135°-136° C. The second crop was submitted to elemental analysis.

Workup

  1. temperaturewas cooled in an ice-bath
  2. stirringStirring
  3. waitwas continued for 3.25 hours at ice-bath
  4. filtrationtemperature, and then the reaction mixture was filtered
  5. additionThe filtrate was poured onto a mixture of 3N hydrochloric acid and water, which
  6. filtrationThe solid was recovered by filtration
  7. customthe gum was recovered by decantation
  8. customThe gum was triturated under isopropanol-water giving further solid material, which
  9. filtrationwas also recovered by filtration
  10. extractionextracted with hot benzene
  11. customleaving a dark, gummy residue
  12. customevaporated in vacuo
  13. customthe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-7a9fd63de3ee47a492b1acb1fc071c05
Source dataset
uspto-grants-1989_02
Patent number
US04808601

Reaction notes

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