nifurzide

Originator

Ricridene,Anphar,Switz.,1981

Definition

ChEBI: Nifurzide is a member of thiophenes and a C-nitro compound.

Manufacturing Process

(a) Ethyl-5-nitro-2-thiophene carboxylate:
17.4 g (mol/10 = 17.31 g) of 5-nitrothiophene carboxylic acid are dissolved in 85 ml of absolute ethanol. A stream of gaseous hydrochloric acid is caused to enter the boiling solution to the point of saturation, and for 5 hours. Evaporation to dryness takes place and then the solid residue is washed with a sodium bicarbonate solution. It is suction-filtered and washed with water. After drying, there are obtained 17.7 g of a yellow product with a melting point of 63°C to 65°C and the yield is 88% (theoretical yield = 88%).
The N'-(5'-nitro-2'-thenoyl)hydrazide is prepared by reacting hydrazine with ethyl 5-nitro-2-thiophene carboxylate.
(b) 6.3 g (mol/30 = 6.5 g) of N1-[5'-nitro-2'-thenoyl]hydrazide are dissolved in 100 ml of dry tetrahydrofuran. 5.6 g (mol/30 = 5.55 g) of 5-nitro-2-furyl acrolein in 56 ml of tetrahydrofuran are added. Heating under reflux takes place for 1 hour and, 25 minutes after starting the heating, the crystallization commences; the crystals are suction-filtered, washed with ether and dried. There are obtained 7.9 g (yield 70%-theoretical yield = 11.2 g) of a yellow solid of melting point 235°C to 236°C.
Recrystallization (tepid dimethylformamide + ether) leaves the melting point unchanged.

Therapeutic Function

Antibacterial, Antidiarrheal