Reaction #95217

Reaction equation

5-amino-3-trichloromethyl-1,2,4-thiadiazole

3-nitrobenzoyl chloride

→

pure product

Yield 69.1%

5-(3-Nitrobenzamido)-3-Trichloromethyl-1,2,4-Thiadiazole

Yield 69.1%

Solvents

xylene

Conditions

Workup

1. 1
   Temperatureat reflux for 20 hours
2. 2
   OtherUnreacted starting amino compound was recovered
3. 3
   Temperatureby cooling the reaction mixture
4. 4
   Filtrationfiltering the resulting precipitate
5. 5
   ConcentrationThe filtrate was concentrated in vacuo
6. 6
   Otherthe residue recrystallized from xylene
7. 7
   WashAfter washing with petroleum ether

Procedure

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.

Source