Acetic Anhydride → HCID 13957976, compound

HRID 2308710Notes

Reaction equation

HRID 2308710 reaction equation
[C:1]1([C:6]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:17])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>CN(C)C=O.CN(C1C=CN=CC=1)C>[C:18]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]([C:6](=[O:7])[C:1]2[S:5][CH:4]=[CH:3][CH:2]=2)[C:9]1=[O:17])(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 13565654HCID 13565654, compound

Product 1

HCID 13957976HCID 13957976, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 486 mg (2.0 mmole) of 3-(2-thenoyl)-2-oxindole in 4 ml of N,N-dimethylformamide was added 538 mg (4.4 mmole) of 4-(N,N-dimethylamino)pyridine. The resulting mixture was cooled in an ice-bath, and then a solution of 225 mg (2.2 mmole) of acetic anhydride in 2 ml of N,N-dimethylformamide was added dropwise, with stirring during about 1 minute. The cooling bath was removed and stirring was continued for 1 hour, and then the reaction mixture was poured onto a mixture of 50 ml of water and 1.7 ml of 3N hydrochloric acid. The resulting mixture was cooled in an ice-bath, and the solid was recovered by filtration. This afforded 528 mg of a yellow solid. The yellow solid was recrystallized from ca. 15 ml of ethanol, giving 300 mg of the title compound as yellow crystals, m.p. 139°-140° C.

Workup

  1. temperatureThe resulting mixture was cooled in an ice-bath
  2. customThe cooling bath was removed
  3. stirringstirring
  4. waitwas continued for 1 hour
  5. additionthe reaction mixture was poured onto a mixture of 50 ml of water and 1.7 ml of 3N hydrochloric acid
  6. temperatureThe resulting mixture was cooled in an ice-bath
  7. filtrationthe solid was recovered by filtration
  8. customThe yellow solid was recrystallized from ca. 15 ml of ethanol

Sources & evidence

ORD record
ord-97db26a382c547159b9353883b404c16
Source dataset
uspto-grants-1987_09
Patent number
US04690943

Reaction notes

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