Hydrochloric Acid → HCID 13910344, compound

HRID 2414086Notes

Reaction equation

HRID 2414086 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.[C:22](OC(=O)C)(=[O:24])[CH3:23].Cl>CN(C)C=O.CN(C1C=CN=CC=1)C>[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:22](=[O:24])[CH3:23])[C:13]1=[O:21])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 13910502HCID 13910502, compound

Product 1

HCID 13910344HCID 13910344, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred slurry of 841 mg (3.0 mmole) of N-benzoyl-2-oxindole-1-carboxamide in 5 ml of N,N-dimethylformamide was added 806 mg (6.6 mmole) of 4-(N,N-dimethylamino)pyridine. Stirring was continued for a few minutes, and then the slurry was cooled in an ice-bath and a solution of 337 mg (3.3 mmole) of acetic anhydride in 2 ml of N,N-dimethylformamide was added dropwise. Stirring was continued for 1 hour, and then the reaction mixture was poured onto a mixture of 65-70 ml. of ice-water and 2.2 ml of 3 N hydrochloric acid. The solid which precipitated was recovered by filtration. It was recrystallized from ethanol to give 385 mg of the title compound as tan crystals, mp 198° C.

Workup

  1. waitwas continued for a few minutes
  2. temperaturethe slurry was cooled in an ice-bath
  3. stirringStirring
  4. additionthe reaction mixture was poured onto a mixture of 65-70 ml
  5. customThe solid which precipitated
  6. filtrationwas recovered by filtration
  7. customIt was recrystallized from ethanol

Sources & evidence

ORD record
ord-acc5cd7927aa4a8bb11b2b41d8d1591b
Source dataset
uspto-grants-1988_01
Patent number
US04721712

Reaction notes

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