3,5-Dinitrobenzoyl chloride → 5-(3,5-Dinitrobenzamido)-3-Trichloromethyl-1,2,4-Thiadiazole

HRID 66941

Reaktionsgleichung

Reaktionsgleichung von HRID 66941
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)[C:17](Cl)=[O:18])([O-:13])=[O:12]>C1(C)C=CC=CC=1>[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)[C:17]([NH:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1)=[O:18])([O-:13])=[O:12]

Komponenten

4

Edukt 2

HCID 74323,5-Dinitrobenzoyl chlorideHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Produkt 1

HCID 130415205-(3,5-Dinitrobenzamido)-3-Trichloromethyl-1,2,4-ThiadiazoleAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A solution of 10.9 g (0.05 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 12.6 g (0.055 mole) 3,5-dinitrobenzoyl chloride in 200 ml toluene was refluxed for 20 hours. The crude product precipitated from the reaction mixture upon cooling to -10° C. After isolation by filtration, the residue was washed with hot petroleum ether and finally recrystallized from methylene chloride to give 17.5 g (85% yield) of pure product; m.p. 197° C.

Aufarbeitung

  1. customThe crude product precipitated from the reaction mixture
  2. filtrationAfter isolation by filtration
  3. washthe residue was washed with hot petroleum ether
  4. customfinally recrystallized from methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-8e93b465b8fa4b39bec5f67f154ba6ef
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343945

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