Carbon Disulfide → HCID 178474076, Verbindung

HRID 1242045

Reaktionsgleichung

Reaktionsgleichung von HRID 1242045
[S].Cl[C:3]1[CH:12]=[CH:11][C:6]([NH:7][C:8](=[O:10])[CH3:9])=[CH:5][C:4]=1[N+:13]([O-])=O.[C:16](=[S:18])=[S:17].COS(OC)(=O)=O>O>[C:8]([NH:7][C:6]1[CH:11]=[CH:12][C:3]2[S:17][C:16]([SH:18])=[N:13][C:4]=2[CH:5]=1)(=[O:10])[CH3:9]

Komponenten

6

Edukt 4

HCID 6348Carbon DisulfideHCID 6497Dimethyl SulfateHCID 79672N-(4-Chloro-3-nitrophenyl)acetamideHCID 5362487Sulfur

Produkt 1

HCID 178474076HCID 178474076, VerbindungAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of Na2S.9H2O (65 g, 0.28 mol), sulfur (25 g, 0.78 mol) and water (150 mL) were heated with stirring at 90° C. for 10 min, and then poured into a flask charged with the above 4′-chloro-3′-nitroacetanilide (21.5 g, 0.10 mol). The resulting mixture was heated at 80° C. for 10 min, and then CS2 (12 mL, 0.2 mol) was added dropwise while maintaining a gentle reflux. The resulting mixture was heated at 90° C. for 7 h. The solids were collected by filtration, washed with water and dilute HCl solution. The solids were taken up in water, and the solution was made alkaline with solid NaOH. The solution was filtered, and the filtrate was acidified with conc HCl. The precipitates were collected by filtration, washed with water, and dried under high vacuum. The crude product was suspended in cold water (200 mL) and solid Na2CO3 was added to obtain pH 13. Dimethylsulfate was added to the above milky solution, and the resulting mixture was stirred at ambient temperature for 3 h. The solids were collected by filtration, washed with water, and dried under high vacuum to yield the title compound (12.4 g, 55%).

Aufarbeitung

  1. temperaturewere heated
  2. additionpoured into a flask
  3. temperatureThe resulting mixture was heated at 80° C. for 10 min
  4. temperaturewhile maintaining a gentle reflux
  5. temperatureThe resulting mixture was heated at 90° C. for 7 h
  6. filtrationThe solids were collected by filtration
  7. washwashed with water and dilute HCl solution
  8. filtrationThe solution was filtered
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with water
  11. customdried under high vacuum
  12. additionsolid Na2CO3 was added
  13. customto obtain pH 13
  14. stirringthe resulting mixture was stirred at ambient temperature for 3 h
  15. filtrationThe solids were collected by filtration
  16. washwashed with water
  17. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-063a9fce41d4491781eb5bfa2fff25b5
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115640B2

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