134 ACYLATION OF AROMATIC AMINES 425 13.4, Acylation of aromatic amines: obtention of acetanilide with acetic acid and Zn Estimated Difficulty Ba time lab operations a ocean 13.4.1. Goal To synthesize aromatic amide without using acetic anhydride. es = 13.4.2. Background Acetamides are usually synthesized from an amine (aromatic or aliphatic) with acetic anhydride. Acetic anhydride, a reagent widely used in the Organic Chem- istry laboratories, is irritating to mucous membranes, is corrosive, and has an unpleasant odor that requires work in a fume hood. In addition, it reacts vie olently with water. As an alternative to this procedure, the synthesis of an aromatic amide (acetanilide) is proposed by using acetic acid as the acylating agent, catalyzed with zine. 13.4.3. Procedure In a 100 ml round-bottom flask, prepare a mixture of 10 ml of aniline, 0.5 g of '30 ml of acetic acid. Connect the flask to a water-jacketed con- zin sheep °C for 2h with magnet stirring, denser and heat in a water bath at 60 Jpon completion of the heating time, ‘uty on completion Crenmeyer containing 100 nl of cokd water. Cool the Er. water bath, and stir t th a glass rod. After a ata will begin to form, Remove them by vacumn ith cold water until the odor from acetie acid activated carbon if the product pour the crude reaction mixture eate- Jenmeyer few minutes, acetanilide filtration, and wash the solid wi disappears. Recrystallize from water adding contains eolored impurities (see ref. [18)).426 134 ACYLATION OF AROMATIC AMINES ‘Tuble 13.4: Physico-chemieal properties of the reagents used. “Compound Me Mp. Bp. Density Danger® CC) CC) (emir!) (GHS) Aniline 9813-6 1st 1022p ae ris aay ee er ee Ghcilaovc acd 60051621810 ‘Acetanilide 135.16 113-115 304 - ! = 0.25-0.60 Non-hazardous ‘Tie formation offered in Une Mata Ste Data Sheet (MSDS) should be consulted. %