Pyridine → N-[(4-Methoxyphenyl)carbonothioyl]acetamide

HRID 353963

Reaktionsgleichung

Reaktionsgleichung von HRID 353963
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[S:12])=[CH:9][CH:8]=1.N1C=CC=CC=1>CC(C)=O>[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH:13][C:1](=[O:3])[CH3:2])=[S:12])=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 7368274-Methoxybenzenecarbothioamide

Produkt 1

HCID 13835614N-[(4-Methoxyphenyl)carbonothioyl]acetamideAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

A solution of acetyl chloride (4.69 g, 59.8 mmol) in acetone (20 mL) was added dropwise to a solution of 4-methoxythiobenzamide (5.00 g, 29.9 mmol) and pyridine (4.76 g, 60.1 mmol) in acetone (30 mL). The reaction mixture was heated to reflux for 30 min then poured onto ice water. The resulting precipitate was isolated via filtration and dried under vacuum overnight to provide a light yellow/orange solid (4.52 g, 72%). 1H NMR (400 MHz, CDCl3) δ2.56 (s, 3H), 3.87 (s, 3H), 6.89 (dd, J=6.9, 2.0 Hz, 2H), (dd, J=6.9, 2.0 Hz, 2H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 min
  3. additionthen poured onto ice water
  4. customThe resulting precipitate was isolated via filtration
  5. customdried under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-a446000c981f4df8af9eebcc520453b9
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756372B2

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