Synthesis of acetanilide from aniline organic chemistry duration. Aniline reacts with acetic anhydride to form acetanilide by nucleophilic substitution reaction and the reaction is called acetylation. An introduction to the synthesis of pnitroaniline via a multistep sequence. Acetanilide is synthesized from aniline by acetylating it with acetic anhydride in presence of glacial acetic acid. The preparation used to be a traditional experiment in introductory organic chemistry lab classes, but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical. Francesca mosca abstract in this experiment the main objective was to synthesize acetanilide from aniline and anhydride. This study describes the synthesis of acetaminophen is quite easy by new method via diazotization reaction. We have developed an improved synthesis of acetanilide from nitrohenzene. The chemistry of sulphonamides has been dealt exhaustively by lednicer and mitscher 64 and by korger 65.
Preparation of acetanilide chemistry practicals class 12. In this case, paminophenol, the amine, is treated with acetic anhydride to form acetaminophen pacetamidophenol, the amide. It was then believed, however, that all compounds having a hydroxyl group on a benzene ring that is, phenols were toxic. Preparation of acetanilide college of science chemistry department 1 preparation and purification of acetanilide purpose. This three step reaction sequence encorporates a number of features important to our study of synthetic organic chemistry. Guma university of anbar college of science received. Recrystallization is just one of the many methods used to purify compounds. Compounds obtained from natural sources, or from reaction mixtures, almost always contain impurities. Thus the intermediate obtained from this sample is of good quality. Acetanilide is a white organic solid compound used primarily in organic synthesis. The nitration of a benzene ring is an electrophilic aromatic substitution reaction, andits general mechanism is summarized in figure 2.
Preparationrecrystallization of acetanilide mendelset. Acetylation of aniline experiment chemistry libretexts. Nphenylacetamide, acetanilide and acetanil are other names of this compound. Allow the reaction mixture to stir for an additional 510 min, during which time most or all of the magnesium metal should be gone. Why do you use acetanilide rather than aniline in the.
In addition to providing a great example of the synthetic utility of these reactions, the synthesis demonstrates the use of protecting group chemistry, and taking advantage of steric and. What is the function of glacial acetic acid for preparation. After the reaction is completed, allow the reaction flask to stir at room temperature for 30 minutes. Reaction mixture should first be cooled and then poured in icecold water otherwise hydrolysis of acetanilide may take place. Acetic acids function while making acetanilide depends on the synthetic route you have chosen. The first step of the reaction involved in the donation of an electron pair by the acetanilide to the eletrophile, the nitronium ion.
Decolorization, filtration, crystallization, craig tube use, preparation of an amide preparation of acetaminophen involves treating an amine with an acid anhydride to form an amide. Nh 2 hn aniline o acetanilide ch 3co 2o ch 3co 2na the purpose of this step is to protect the amine functional group from entering into unwanted reactions during the subsequent chlorosulfonation and amination steps. Preparation of acetanilide from aniline pharmadhunia. Acetanilide can be produced by reacting acetic anhydride with aniline. The customary route involves acetic anhydride and aniline and results in the corresponding formation of acetic acid as a byproduct. They are then able to compare the melting points of the impure and recrystallized acetanilide. Synthesis and characterization of acetaminophen paracetamol. Upon addition of chlorosulfonic acid to acetanilide, a reaction was observed, n hc ch3 o.
Acetanilide, synthetic organic compound introduced in therapy in 1886 as a feverreducing drug. Neutralize with 10% naoh, cool and filter the yellow crystalline product on a buchner funnel. The sodium acetate acts as a base and reacts with the hcl to produce acetic. Preparation of acetanilide from aniline pharmadunia. Collect the infrared spectrum of the part 1 product, acetanilide, and the unknown starting material and product from part 2. Prolonged heating and use of excess of acetic anhydride should be avoided. Its effectiveness in relieving pain was discovered soon thereafter, and it was used as an alternative to aspirin for many years in treating such common complaints as headache, menstrual cramps, and. H 2 so 4 to the viscous reaction mixture drop by drop with constant stirring, so that the temperature of the mixture does not rise above 10c. Acetanilide strongly activating bromobenzene deactivating 4nitroacetanilide bromobenzene deactivating chlorobenzene deactivating mixture of bromo and chloro products acetanilide strongly activating toluene activating 4nitroacetanilide acetanilide strongly activating nitrobenzene very strongly deactivating 4nitroacetanilide. Acetanilide is prepared from aniline by acetylating it with acetic anhydride in the presence of glacial. Add 5 ml of chlorosulfonic acid corrosive and reacts violently with water a few drops at a time using a pasteur pipet no metal needles. Each reaction produces a product that is used in the next one.
Nacetylarylamine is an odourless solid chemical of leaf or flakelike appearance. Aniline can be easily converted to acetanilide by acetylation reaction using acetic anhydride in the presence of sodium acetate. After 10 min the reaction should subside and almost all of the acetanilide will have dissolved. Recrystallization is the most convenient method for purifying organic compounds that are solids at room temperature. The total synthesis of sulfanilamide from benzene can be carried out in six steps using reactions that are very familiar to intermediate level organic chemists. Recrystallization university of massachusetts amherst. Not giving equivalents, temperatures, solvents, reaction times etc. Pour the reaction mixture into a 250 ml beaker containing 100 ml of cold tap water.
Synthesis of pbromoacetanilide from acetanilide labmonk. Allow the reaction mixture to cool to room temperature. Each product should be cospotted against the starting material for each reaction, respectively, and against each other. Synthesis of acetamides from aniline and substituted anilines. They could have at least provided the number of equivalents during the bromination. Next, we determine the mole ration of aniline to acetanilide. There are several key steps involved in the nitration. Take your hr comms to the next level with prezi video. Reaction of the latter with the appropriate arylamine affords the. Paracetamol acetaminophen, acetanilide and phenacetin belong to a class of antipyretic analgesics. Nacetylarylamine has analgesic and feverreducing properties. Finally, we convert the moles of acetanilide into grams of acetanilide. The impurities may include some combination of insoluble, soluble and colored impurities.
The complete synthesis of sulfanilamide from benzene, experimental laboratory manual for organic chemistryii, 2012, pg. Generally the sulpha drugs are prepared by two alternative routes scheme 1. Stir the reaction mixture carefully during addition. We can and should put this all together into one calculation. Bromination is an electrophilic substitution reaction on an aromatic ring.
Sulfa antibiotics synthesis of sulfanilamide intoroduction. Duisberg devised a scheme of structural modification of paminophenol to get the compound phenacetin. Organic synthesis is a method of preparation of organic compounds. Acetanilide is prepared from aniline using an acetylation reaction. The first method uses acetanilide 39 as the starting material, which is chlorosulphonated to get 4acetamidobenzenesulphonyl chloride 40. Synthesis of pnitroaniline from acetanilide labmonk. Place 2 g of dry acetanilide in a dry 25ml erlenmeyer flask. So, simply mixing them together does not result in the efficient formation of. In the presence of strong acids, oximes can undergo molecular rearrangement to form amides via the beckmann rearrangement. It was used in the past to treat fever and headache and was known as antifebrin by its brand name.
It is also known as acetanilide, nphenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name antifebrin. Aniline or phenylamine is a primary amine and basic in nature. This prevents the formation of polybrominated site products. Zinc reduces the coloured impurities in the aniline and also prevents its oxidation during the reaction. Synthesis and characterization of acetaminophen paracetamol from acetanilide by diazotization reaction and comparing with crude. An amine may lead to di and tri substituted products. Acetanilide antifebrin was the first to have been introduced in the year 1886, but its use was limited at high doses due to toxic side effects of methemoglobinemia and jaundice. Through the use of electrophilic aromatic substitution, acetanilide is nitrated to nitroacetanilide.
An introduction to the synthesis of pnitroaniline via a. Multistep synthesis refers to a sequence of reactions designed to produce a specific molecule as the final outcome. Place 30 g of pnitroacetanilide and 150 ml of 70% h2so4 prepared by adding 100 ml conc. The second step in the synthesis of pnitroaniline is the preparation of acetanilide from acetophenone oxime scheme 2.
Scheme 1 synthesis of acetanilide today you will be given an impure acetanilide sample and will be expected to purify the acetanilide through recrystallization. Water is the only byproduct in hbr h2o2 method and in nabr nabro3. The overall reaction for the nitration of methyl benzoate. Jan 12, 2018 acetic acids function while making acetanilide depends on the synthetic route you have chosen. Sep 15, 2014 please use one of the following formats to cite this article in your essay, paper or report. Folic acid can also be synthesized in the laboratory1 the synthesis and bioassay of sulfanilamide this experiment is the synthesis and bioassay of sulfanilamide, starting acetanilidewith acetanilide. Synthesis of 2, 4, 6tribromoaniline from aniline organic chemistry aniline undergoes nucleophilic substitution with bromine, even in cold. Journal of chemical and pharmaceutical research, 2016, 8. Please use one of the following formats to cite this article in your essay, paper or report. In the synthesis of acetanilide the hydrochloride salt of aniline is used in order to increase the solubility in water. It is concerned with the preparation of organic compounds through organic reactions. Synthesis of acetanilide using acetic acid by conventional and green method duration. If traces of mg metal are left, they will dissolve when hcl is added in step 11. Metabolism of paracetamol acetaminophen, acetanilide and.
Aug 09, 2015 synthesis of a bromoalkane nbromopropane duration. In this reaction, aniline acts as the nuclepohile and acyl ch 3 co group from acetic anhydride acts as the electrophile. In the first step the acetanilide was nitrated with nitric acid in the presesnce of sulphuric acid to form pnitroacetanilide, and then it was reduced to. From our reaction scheme, its clear that for every 1 mole of aniline we use we produce 1 mole of acetanilide, so the ratio is 1to1. In the first step the acetanilide was nitrated with nitric acid in the presesnce of sulphuric acid to form pnitroacetanilide, and then it was reduced to pamino derivative, then it was converted. To prepare pbromoacetanilide from acetanilide by bromination reaction.
122 1535 1589 9 1337 1462 420 100 1039 680 586 1246 1556 472 948 1057 433 392 88 1029 1349 1398 1047 21 1333 56 112 447 680 583 1494 924 69 1412 700