p-Toluenesulfonic acid → HCID 54126959, Verbindung

HRID 636671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636671
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[CH:7]=O.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].N1CCCC1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[Na]>C1(C)C=CC=CC=1>[C:9]([C:11](=[CH:7][C:6]1[S:5][N:4]=[N:3][C:2]=1[CH3:1])[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

Komponenten

7

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 7764Ethyl cyanoacetateHCID 31268PyrrolidineHCID 27712924-Methyl-1,2,3-thiadiazole-5-carbaldehydeHCID 5360545Sodium

Produkt 1

HCID 54126959HCID 54126959, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 50 ml of toluene were added 1.5 g (12 mmol) of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde, 1.5 g (13 mmol) of ethyl cyanoacetate, 0.40 g (6.0 mmol) of pyrrolidine and 0.20 g (1.2 mmol) of tosylic acid. In a reactor equipped with a Dean-Stark dehydrating apparatus, the mixture obtained above was stirred for 2 hours with heating under reflux. After the reaction was completed, a saturated aqueous solution of sodium Achloride was added to the reaction mixture, the objective product was extracted with ethyl acetate, the organic layer was washed successively with dilute hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 3:1 mixture of n-hexane and ethyl acetate. Thus, 0.73 g of the objective compound was obtained.

Aufarbeitung

  1. customIn a reactor equipped with a Dean-Stark
  2. customthe mixture obtained
  3. temperaturewith heating
  4. temperatureunder reflux
  5. extractionthe objective product was extracted with ethyl acetate
  6. washthe organic layer was washed successively with dilute hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. addition3:1 mixture of n-hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4cbf54cf4f8d4370bcf243985507cb48
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194444B1

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