Sulfa Drugs Lab Report
Introduction:
Sulfa drugs are any member of a group of synthetic antibiotics containing the sulfanilamide molecular structure (Figure 1). Sulfa drugs were the first class of antibiotics to treat and prevent bacterial infection in humans. Sulfa drugs have been used less frequently due to improved antibiotics that are more effective, have less side effects, and decreased drug resistance.1, 2 Sulfonamides are still used today as an anti-bacterial medication and for the prevention of burns. The antibacterial effects of sulfonamides were first observed in 1932 by German bacteriologist and pathologist Gerhard Domagk. Domagk studied the effects of red dye Prontosil (Figure 1) on Streptococcus infection in mice by using competitive inhibition to stop the production of the bacteria of which, the …show more content…
To get to aniline, tin metal acts as a reducing agent and is oxidized to SnCl4. The purification of crude aniline is done by distillation and extraction. Aniline can be converted to acetanilide by acetylation reaction using acetic anhydride with sodium acetate. This step protects the amine functional group from doing unwanted reactions during chlorosulfonation and amination steps. The chlorosulfonyl group attacks in the para position to the acetamide group, by electrophilic aromatic substitution. Sulfonic acid is converted to 4-acetamidobenzenesulfonyl chloride by reacting with chlorosulfonic acid. The 4-acetamidobenzenesulfonyl chloride is converted to sulfonamide by reacting with aqueous ammonia. Acetamide group of the 4-acetamidobenzenesulfonly is hydrolyze under acidic conditions. Acidic hydrolysis solution is neutralized with sodium carbonate to isolate sulfanilamide. This method takes longer than the original method (scheme 1), because TFAA in the original method speeds up the rate of the reaction. Neither of the reactions are extremely environmentally
Sulfa drugs are any member of a group of synthetic antibiotics containing the sulfanilamide molecular structure (Figure 1). Sulfa drugs were the first class of antibiotics to treat and prevent bacterial infection in humans. Sulfa drugs have been used less frequently due to improved antibiotics that are more effective, have less side effects, and decreased drug resistance.1, 2 Sulfonamides are still used today as an anti-bacterial medication and for the prevention of burns. The antibacterial effects of sulfonamides were first observed in 1932 by German bacteriologist and pathologist Gerhard Domagk. Domagk studied the effects of red dye Prontosil (Figure 1) on Streptococcus infection in mice by using competitive inhibition to stop the production of the bacteria of which, the …show more content…
To get to aniline, tin metal acts as a reducing agent and is oxidized to SnCl4. The purification of crude aniline is done by distillation and extraction. Aniline can be converted to acetanilide by acetylation reaction using acetic anhydride with sodium acetate. This step protects the amine functional group from doing unwanted reactions during chlorosulfonation and amination steps. The chlorosulfonyl group attacks in the para position to the acetamide group, by electrophilic aromatic substitution. Sulfonic acid is converted to 4-acetamidobenzenesulfonyl chloride by reacting with chlorosulfonic acid. The 4-acetamidobenzenesulfonyl chloride is converted to sulfonamide by reacting with aqueous ammonia. Acetamide group of the 4-acetamidobenzenesulfonly is hydrolyze under acidic conditions. Acidic hydrolysis solution is neutralized with sodium carbonate to isolate sulfanilamide. This method takes longer than the original method (scheme 1), because TFAA in the original method speeds up the rate of the reaction. Neither of the reactions are extremely environmentally