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To generate the mono-substituted product, a protection with acetyl chloride is required: Aniline can react with bromine even in room temperatures in water. Acetyl chloride is added to prevent tribromination. The reaction to form 4-bromoaniline is to protect the amine with acetyl chloride, then hydrolyse back to reform aniline.
Aniline reacts with acyl chlorides or carboxylic anhydrides to give anilides. For example, reaction of aniline with acetyl chloride provides acetanilide ( CH 3 −CO−NH−C 6 H 5 ). At high temperatures, aniline and carboxylic acids react to give anilides.
Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. [4]Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).
Phenylhydrazine is prepared by reacting aniline with sodium nitrite in the presence of hydrogen chloride to form the diazonium salt, which is subsequently reduced using sodium sulfite in the presence of sodium hydroxide to form the final product. [6]
Benzylamine reacts with acetyl chloride under Schotten-Baumann conditions to form N-benzylacetamide. Schotten–Baumann reaction also refers to the conversion of acid chloride to esters. The reaction was first described in 1883 by German chemists Carl Schotten and Eugen Baumann. [1] [2]
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids (R−C(=O)OH). A specific example of an acyl chloride is acetyl chloride, CH 3 COCl.
Benzylamine reacts with acetyl chloride to form N-benzylacetamide. Isoquinolines can be prepared from benzylamine and glyoxal acetal by an analogous approach known as the Schlittler-Müller modification to the Pomeranz–Fritsch reaction. This modification can also be used for preparing substituted isoquinolines. [11] Synthesis of HNIW from ...
The following synthesis, developed by an individual under the pseudonym of Siegfried, involves the reductive amination of N-phenethyl-4-piperidinone (NPP) with aniline to make to 4-ANPP. This product is reacted with propionyl chloride or acetyl chloride to form either fentanyl or acetylfentanyl.