Ricridene,Anphar,Switz.,1981
ChEBI: Nifurzide is a member of thiophenes and a C-nitro compound.
(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.
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