Water → 5-Amino-3-(methylthio)-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide

HRID 324375

Reaktionsgleichung

Reaktionsgleichung von HRID 324375
[CH3:1][S:2][C:3](=[C:6]([C:10]#[N:11])[C:7]([NH2:9])=[O:8])SC.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:14]=1[NH:21][NH2:22].O>CO>[NH2:11][C:10]1[N:21]([C:14]2[C:13]([Cl:12])=[CH:18][C:17]([Cl:19])=[CH:16][C:15]=2[Cl:20])[N:22]=[C:3]([S:2][CH3:1])[C:6]=1[C:7]([NH2:9])=[O:8]

Komponenten

5

Edukt 3

HCID 962WaterHCID 79234(2,4,6-Trichlorophenyl)hydrazineHCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Produkt 1

HCID 113025915-Amino-3-(methylthio)-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamideAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of bis(methythio)methylenecyanoacetamide (7.800 g, 50 mmol) and 2,4,6-trichlorophenylhydrazine (10.575 g, 50 mmol) in 250 ml of methanol was heated at reflux for 2.5 hours. The mixture was cooled and water was added. Precipitate formed and filtered to give 14.323 g (81.5% yield) of the title compound as a white solid. 1H NMR(CDCl3): 2.6 (s,3H), 5.5(brs, 2H), 7.5(s,2H) ppm. Recrystallization of a small portion of the solid from chloroform gave white crystals; m. p. 198-199° C. Anal. Calc. for C11H9Cl3N4OS: C, 37.57; H, 2.58; N, 15.93; Found: C, 37.54; H, 2.51; N, 15.73.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. temperatureThe mixture was cooled
  4. customPrecipitate formed
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-c13c5fd8e8314a288ea8f87bcf3cb292
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218397B1

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