Oxindole → 3-[(2-Methylmercaptothien-5-yl)methylene]-2-indolinone

HRID 1976180Notes

Reaction equation

HRID 1976180 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH3:11][S:12][C:13]1[S:17][C:16]([CH:18]=O)=[CH:15][CH:14]=1>N1CCCCC1.C(O)C>[CH3:11][S:12][C:13]1[S:17][C:16]([CH:18]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 321710OxindoleHCID 27369975-(Methylsulfanyl)thiophene-2-carbaldehyde

Product 1

HCID 696311263-[(2-Methylmercaptothien-5-yl)methylene]-2-indolinoneYield 90%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture of 134.0 mg of oxindole, 189.9 mg of the 5-methylmercaptothiophene-2-carboxaldehyde, and 3 drops of piperidine in 2 mL of ethanol was stirred at 90° C. for 3 h. After cooling, the precipitate was filtered, washed with cold ethanol, and dried to yield 246.6 mg (90%) of the title compound as a orange solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered
  3. washwashed with cold ethanol
  4. customdried

Sources & evidence

ORD record
ord-56e28b881f4d497d896eb31fc57220aa
Source dataset
uspto-grants-2001_05
Patent number
US06225335B1

Reaction notes

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