Sulfonamides Laboratory: Properties, Identification, and Chemical Reactions

Sulfonamides are compounds that are considered derivatives PABA (para amino benzoic acid ). Organic compounds that have the elements N and S in addition to C, H and O which have chemotherapeutic, diuretic and antidiabetic properties. General formula Sulfonamides are used as chemotherapeutics, antibiotics, disinfectants and diuretics. General Properties of the Sulfonamide group 1. Organoleptic: a. In the form of a solid substance, crystalline form, not hygroscopic, white or slightly yellowish in color b. When exposed to direct sunlight, the color becomes darker c. Almost tasteless or bitter d. No smell 2. It is amphoteric so it is difficult to separate by shaking which is commonly used in organic chemical analysis 3. Solubility: a. Generally insoluble in cold water, soluble in hot water b. Easily soluble in acetic acid except sulfasuccidin, phthasol and elcosine c. Soluble in acetone and alcohol d. Soluble in alkali hydroxide (in salt form) e. Insoluble in ether, CHCl3 4. Test substance + 1-2 drops of DAB HCl → observe the color that occurs, also observe the crystals under a microscope (compare each sulfa) 5. Test substance in test tube + NaOH → neutralize excess alkali with HCl → + CuSO4→ shake/shake → observe the color that occurs (compare each sulfa) 6. Test substance + saturated KBrO solution3+ 1-2 drops of H2SO4concentrated → observe the color that occurs (compare each sulfa) A. Color reaction 1. Erlich A little solid substance is added to the drop plate and then 1-2 drops of DAB HCl reagent are added to form a yellow-orange color. 2. Match reaction Dilute HCl is added to the substance, then a matchstick is dipped into it, an intense orange-yellow color appears. 3. Diazo reaction Substance (±10mg) in 2 drops of HCl 2 A then added with 1 ml of water. To this solution, 2 drops of diazo B (0.9% NaNO solution) were added2) and drop a solution of 0.1 g of β-naphthol in 2 ml of NaOH to form an orange then blood red color. 4. Indophenol A total of 50-100 mg of the substance is dissolved in 2 ml of water, heated until boiling, then 2 drops of NaOH and 2 ml of NaOCl or chlorine solution are added, then 1 drop of phenol is added. 5. Roux reaction The substance is placed on the drip plate then 1 drop of Roux reagent is added, stirred with a stir stick. 6. Reaction of sulfone groups Substance + H2O230% + 1 drop FeCl3+ HNO3and BaCl2or Barium Nitrate → white precipitate BaSO4(Meatball4difficult to dissolve, even in aqua regia). 7. Furfural reaction: towards free amine groups. 1 drop of reagent (furfural 2% in glacial acetic acid) + substance gives a dark red color that immediately changes to purple. All sulfas gave positive results, except sulfasuccidin, pthalazol, septazine. B. Identification by solubility 1. Soluble in water a. The sodium salts b. Sulfonamidum c. Sulfonamides = partially water soluble 2. Pickled with 3% vinegar a. Soluble: Sulfanilamide, Sulfacetamid, Soluseptazin b. Insoluble: Sulfadiazine, Sulfamorazine, Sulfamethazine, Sulfathiazole, Sulfapyridine, 3. Soluble in 96% alcohol. Sulfacetamide, Sulfathiazole Na 4. Insoluble in 96% alcohol. Sulfadiazine Na, Sulfamerazine Na, Sulfamethazine Na, Sulfapyridin Na, and Sulfathiazol Na. 5. Soluble in 7% acetic acid. Sulfanalamide, Sulfacetamid 6. Insoluble in water. soluble in hot water: sulfanilamide, sulfacetamide 7. Insoluble in 10% NaOH. Sulfaguanidine Precipitation/Crystal Reaction Commonly used reagents: Acetone – water, Alcohol – water, Picric acid, Bouchardat, Dragendorf, Cu Complex, Fe Complex, P-DAB HCl, Mayer 5. Implementation of Practicum a. Tools and materials Sulfonamide compound reagent, test tube, dropper pipette, tube rack, glass object, cover glass, microscope, spirit lamp, sublimation ring b. Work procedures 1. Sulfacetamide a. Roux reaction: emerald green b. Substance + p-DAB-HCl → dark green soon orange yellow c. Substance + KBrO3→ orange yellow → dark brown d. Substance ± 20 mg + 0.5 ml NaOH 0.1 N + 2 drops CuSO4→↓greenish yellow/blue solution, when shaken → brown e. Esterification: Substance + ethanol+ H2SO4concentrated → ethyl acetate f. Indofenol reaction: green/brick red precipitate g. Zwikker reaction: Blue-violet h. Match: Orange i. Parri reaction: positive/green precipitate j.Crystal Reaction : p-DAB-HCl, water acetone, picric acid. 2. Sulfadiazine a. Matches: yellow orange b. Roux reaction: immediate purple → purple/blue/yellow/green c. Substance + p-DAB-HCl → dark yellow, orange d. Substance + CuSO4→ purple + acetone→ purple black e. Substance + water, heat + NaOH 2 drops, cool + CuSO41 drop, neutralize with dilute HCl → Yellow then violet f. Test substance + Parri reagent → purple green color g. Substance + Alcohol + Parri + NH4OH 1 drop → Dark red h. Substance + Vanillin + H2SO4→ brown i. Substance + 1 ml H2SO4dilute + 1 drop of KBrO reagent3saturated → yellow orange brown red j. Substance in 10 ml water + 1 ml NaOH 0.1 N + 0.5 ml CuSO4→ yellow green sediment let stand → brown k. Indofenol reaction: rosa red/brick red l. Zwikker: Pink m. Pyrolysis reactionA: red brown-green n. Raybin reaction: substance+ H2SO4concentrated →carmine red + glacial acetic acid + NH4OH→ fluorescent blue yellow green o. Esterification: Substance + ethanol+ H2SO4concentrated → ethyl acetate p.Crystal Reaction : sublimation, water acetone, picric acid, bouchardat, dragendorf