Benzoyl chloride, 3-nitro- → 5-(3-Nitrobenzamido)-3-Trichloromethyl-1,2,4-Thiadiazole

HRID 66939

Reaktionsgleichung

Reaktionsgleichung von HRID 66939
[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]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18])([O-:13])=[O:12]>C1(C)C(C)=CC=CC=1>[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][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 8495Benzoyl chloride, 3-nitro-HCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Produkt 1

HCID 130415185-(3-Nitrobenzamido)-3-Trichloromethyl-1,2,4-ThiadiazoleAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A solution of 21.8 g (0.1 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 18.6 g (0.1 mole) 3-nitrobenzoyl chloride in 250 ml xylene was heated at reflux for 20 hours. Unreacted starting amino compound was recovered by cooling the reaction mixture and filtering the resulting precipitate. The filtrate was concentrated in vacuo and the residue recrystallized from xylene. After washing with petroleum ether, 25.4 g (69% yield) of pure product was obtained; m.p. 198° C.

Aufarbeitung

  1. temperatureat reflux for 20 hours
  2. customUnreacted starting amino compound was recovered
  3. temperatureby cooling the reaction mixture
  4. filtrationfiltering the resulting precipitate
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue recrystallized from xylene
  7. washAfter washing with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-de6e7a9e35cd4ea48025e0a704ebed64
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343945

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