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Benzaldehyde oxime undergoes Beckmann rearrangement to form benzamide, catalyzed by nickel salts [3] or photocatalyzed by BODIPY. [4] Its dehydration yields benzonitrile. It can be hydrolyzed to regenerate benzaldehyde. [5]
synthesis of benzamide from benzoyl chloride and a phenethylamine; synthesis of flutamide, a nonsteroidal antiandrogen; acylation of a benzylamine with acetyl chloride (acetic anhydride is an alternative) In the Fischer peptide synthesis (Emil Fischer, 1903), [6] an α-chloro acid chloride is condensed with the ester of an amino acid.
Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis. [3] It is a precursor to diphenylmethanimine via reaction with phenylmagnesium bromide followed by methanolysis.
Hippuric acid, the benzamide derivative of glycine, cyclizes in the presence of acetic anhydride, condensing to give 2-phenyl-oxazolone. [3] This intermediate also has two acidic protons and reacts with benzaldehyde, acetic anhydride and sodium acetate to a so-called azlactone. This compound on reduction gives access to phenylalanine. [4]
Print/export Download as PDF; Printable version; In other projects ... Ammonium benzoate can be dehydrated to form benzamide. References
Benzamide is an organic compound with the chemical formula of C 7 H 7 NO. It is the simplest amide derivative of benzoic acid . In powdered form, it appears as a white solid, while in crystalline form, it appears as colourless crystals. [ 5 ]
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Benzophenone imine can also be synthesized by addition of phenylmagnesium bromide to benzonitrile followed by careful hydrolysis (lest the imine be hydrolyzed): [3] C 6 H 5 CN + C 6 H 5 MgBr → (C 6 H 5) 2 C=NMgBr (C 6 H 5) 2 C=NMgBr + H 2 O → (C 6 H 5) 2 C=NH + MgBr(OH) This method is known as Moureu-Mignonac ketimine synthesis. [4]