3,4-Dimethoxybenzonitrile → 3,4-Dimethoxythiobenzamide

HRID 1421944

Reaktionsgleichung

Reaktionsgleichung von HRID 1421944
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:6]#[N:7].C(N)(=[S:15])C>Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:6]([NH2:7])=[S:15]

Komponenten

4

Edukt 2

HCID 748423,4-DimethoxybenzonitrileHCID 2723949Thioacetamide

Produkt 1

HCID 27584903,4-DimethoxythiobenzamideAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10920465N,N-dimethylformamide;hydrochlorideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

25 g of 3,4-dimethoxybenzonitrile and 23 g of thioacetamide were dissolved in 120 ml of 10% hydrochloric acid-DMF. The solution was heated at 90° C. for 3 hours. The solution was further heated at 130° C. for 5 hours to conduct a reaction. The solvent was removed by distillation. The residue was washed twice with 100 ml of diethyl ether. Similar washing was conducted with 100 ml of water. The resulting crystals were collected by filtration and dried. Recrystallization from methanol was conducted to obtain 18.7 g of 3,4-dimethoxythiobenzamide as light brown columnar crystals.

Aufarbeitung

  1. temperatureThe solution was further heated at 130° C. for 5 hours
  2. customa reaction
  3. customThe solvent was removed by distillation
  4. washThe residue was washed twice with 100 ml of diethyl ether
  5. washSimilar washing
  6. filtrationThe resulting crystals were collected by filtration
  7. customdried
  8. customRecrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-faf2b22a52924dcca2aa946d5eed631b
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06080764

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