Sulfanilamide Synthesis Lab Report

The product obtained had a melting point of approximately 107 °C and a weight of .324 grams. Some of the product would not dissolve in water and so was removed through vacuum filtration, which left .141 g not dissolved in solution. It took 13.2 mL of sodium hydroxide to turn the solution of the product dissolved in water pink. A molecular weight of 138.63 g/mol was calculated from the data. These results indicate that the product was 2-methylbenzoic acid, the Grignard reagent was 2-methylphenylmagnesium bromide, and the unknown bromide solution was 2-methylbromobenzene. Calculations showed that the limiting reagent of the Grignard preparation was magnesium and that the experiment had a 23.13 % yield.

The mixture was heated at 120°C using an aluminum block and was stirred gently. After all of the solid dissolved, it was heated for 20 additional minutes to ensure the reaction was complete.

In a 25-mL round-bottom flask, 1-chlorobutane (5 mL, 4.32 g, 0.046 mol), sulfuryl chloride (1.6 mL, 2.7 g, 0.02 mol), 2,2’-azobis-(2-methylpropionitrile) (0.03 g), and a boiling chip were added. After a condenser and gas trap were attached to the flask, the mixture was heated to a gentle reflux in a steam bath for 20 min. The flask was then allowed to cool down quickly in an ice bath for a short time before a second portion of the 2,2’-azobis-(2-methylpropionitrile) (0.03 g) was added to the flask. The mixture was refluxed for another 10 min. before the flask was cooled in a beaker of water. The reaction mixture was then poured into a small separatory funnel already filled with water (10 mL),

Salbutamol is sold in its sulphate form and is marketed as a racemic product. According pharmaceutical chemistry this means that in it, it has 50% of the R enantiomer and 50% of the S enantiomer. However, only the R enantiomer is active at the β receptors. It is thought that the S enantiomer is inactive or causes adverse effects. Because of this, the pure R enantiomer was marketed – levalbuterol.

Once cooled, the mixture was then transferred to a separatory funnel using the funnel while avoiding adding the boiling chip. 10 ml of water was then added to the mixture. The mixture was gently shaken and the phases were allowed to separate. The funnel was then unstopped and the lower aqueous phase was drained into a beaker. 5 ml of 5% aqueous NaHCO3 was added and then shaken gently. A great deal of caution was taken into consideration because of the production of carbon dioxide gas which caused pressure to develop inside the funnel. The pressure needed to be released so the funnel was vented frequently. The phases were allowed to separate and the lower aqueous phases was drained into the beaker. After draining, 5 ml of saturated NaCl was added to the funnel and then shaken gently. Once again, the phases were allowed to separate and the lower aqueous phase was drained into a beaker. An ester product was produced and was transferred into a 25 ml Erlenmeyer flask. This organic product was then dried over anhydrous Na2SO4 to trap small amounts of water in its crystal lattices thus removing it from the product. Finally the ester was decanted, so that the drying agent was excluded from the final product.

Sulfanilamide, also referred to as sulfa, was a drug sold in powder and tablet form used to treat infections such as pneumonia, meningitis, and strep throat. In the 20th century, these bacterial infections could easily take the life of anyone. That is why sulfanilamide became so popular throughout the country. Sulfanilamide was invented by a German microbiologist, Gerhard Domagk. It was a red dye derivative that he had discovered that would cure the contagion. The drug was safe until a salesman from Bristol, Tennessee recommended that they produce a liquid form of the drug to make swallowing easier. The company’s head pharmacist and chemist was Harold Cole Watkins, he found out that sulfanilamide was soluble in diethylene glycol, commonly found

The beaker was slowly heated on a hot plate with low stirring until most of the stilbene was dissolved. 0.4 g of pyridinium tribromide was measured and added to the beaker after 5 minutes of heating. Small amounts of ethanol were used to clean the sides of the beaker. The beaker was heated for an additional 10 minutes on low temperature. An ice bath was prepared. The beaker was removed from the hot plate and left to cool to room temperature. Once at room temperature, the beaker was placed in the ice bath for 15 minutes. The solid product was collected through vacuum filtration and the product was weighed and a melting point was taken. Waste was disposed of in the correct waste bins and lab bench was cleaned

Aspirin was synthesized by reacting salicylic acid with acetic anhydride in the presence of phosphoric acid, H3PO4, as a catalyst:

Silver sulfadiazine, a white, highly insoluble compound, was first synthesized by Fox in 1968 from silver nitrate and sodium sulfadiazine(45).

Salicylic acid was esterfied using acetic acid and sulfuric acid acting as a catalyst to produce acetylsalicylic acid and acetic acid. The phenol group that will attack the carbonyl carbon of the acetic anhydride is the –OH group that is directly attached to the benzene since it is more basic than the –OH group attached to the carbonyl group. This method of forming acetylsalicylic acid is an esterification reaction. Since this esterification reaction is not spontaneous, sulfuric acid was used as a catalyst to initiate the reaction. Sulfuric acid serves as the acid catalyst since its conjugate base is a strong deprotonating group that is necessary in order for this reaction to be reversible. The need for the strong conjugate base is the reason why other strong acids such as HCl is not used since its conjugate base Cl- is very weak compared to HSO3-. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in

The antibacterial effects of sulfanilamide were first observed in 1932, when German bacteriologist and pathologist Gerhard Domagk noted the effects of the red dye Prontosil on Streptococcus infections in mice. It was later proved by French researchers that the active agent of Prontosil was sulfanilamide, or para-aminobenzenesulfonamide, a product of the body’s metabolism of Prontosil. By the 1940s sulfanilamide was a widely used drug. During World War II white sulfanilamide powders became standard in first-aid kits for the treatment of open wounds, and sulfanilamide tablets were taken to fight intestinal infections. Though the medicine was relatively safe, allergic reactions such as skin rashes, fever, nausea, vomiting, and even mental confusion

After all additional product ceased to form, the reaction mixture was cooled in an ice bath to allow precipitation of benzopinacol. The final product was then filtered off from the solution using a Buchener funnel. Its melting point, yield and infrared spetrum was then obtained.

Purpose The purpose of this experiment was to prepare acetylsalicylic acid, which is aspirin, investigate two of its chemical properties, and measure the purity of the synthesized aspirin. The aspirin was created in an esterification reaction between salicylic acid and acetic anhydride. Using the aspirin that was made from salicylic acid and acetic anhydride, it was tested to see if the salicylic acid in the aspirin acts as a phenolic alcohol or as a carboxylic acid by adding FeCl3 solution.

Sulfa drug is any member of a group of synthetic antibiotics containing the sulfanilamide molecular structure. Sulfa drugs were the first antibiotics to treat and prevent bacterial infections in humans.

Sulfa drugs (sulfonamide) do contain sulfur, but the allergic reaction is not sulfur per se, rather it is the byproduct of sulfonamide metabolism.