Synthesis of N-(4-methylphenyl)benzamide

Preparation of N-(4-methylphenyl)benzamide

Preparation of N-(4-methylphenyl)benzamide

Preparation of N-(4-methylphenyl)benzamide

2 g of finely divided p-toluidine are mixed with 10 ml of a 10% aqueous solution of sodium hydroxide, and 2 ml benzoyl chloride are added gradually to the warm mixture in a corked flask, which is mechanically shaken. Thorough shaking is essential. If any excess of benzoyl chloride remains, it is destroyed by warming with a further quantity of sodium hydroxide solution. The mixture is then poured into water, and the precipitate filtered, dried, and recrystallised from alcohol. Yield almost theoretical, colourless crystals; insoluble in water; m.p. 158° C.

Systematic organic chemistry, by W. M. Cumming, 304, 1937.

IUPAC Name

N-(4-methylphenyl)benzamide

InChI

InChI=1S/C14H13NO/c1-11-7-9-13(10-8-11)15-14(16)12-5-3-2-4-6-12/h2-10H,1H3,(H,15,16)

InChI Key

YUIHXKGKVSVIEL-UHFFFAOYSA-N

Canonical SMILES

CC1=CC=C(C=C1)NC(=O)C2=CC=CC=C2

Depositor-Supplied Synonyms

N-(4-Methylphenyl)benzamide, p-Benzotoluidide, N-p-Tolyl-benzamide, 4′-Methylbenzanilide, Benzamide, N-p-tolyl-, BENZO-p-TOLUIDIDE, Benzamide, N-(4-methylphenyl)-, N-Benzoyl-p-toluidine, Benzoic acid p-toluidide, 582-78-5, YUIHXKGKVSVIEL-UHFFFAOYSA-N, AE-848/00895014, Para-methylbenzanilide, N-(p-tolyl)benzamide, AC1Q2RKS, Maybridge1_004370, AC1L29UV, AC1Q2M8J, SCHEMBL82305, MLS000523601, N-(4-Methylphenyl)benzamide #, CHEMBL1489271, CTK1H0770, HMS553O16, MolPort-000-882-063, HMS2359E23, ZINC164223, NSC17586, EINECS 209-491-8, NSC-17586, STK259692, ZINC00164223, AKOS000277999, MCULE-1741867493, NCGC00245386-01, BAS 04456749, OR052257, OR289166, SMR000122674, AI3-00503, KB-102287, ST50275663

Removed Synonyms

p-Toluoylaniline, 4′-Fluorobutyrophenone, CID68497

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