Synthesis of benzanilide

Preparation of benzanilide

Preparation of benzanilide

Preparation of benzanilide

12 g of aniline are placed in a dish in a fume cupboard, and 10 g of benzoyl chloride are gradually added. Much heat is developed. When cold the product is extracted first with dilute hydrochloric acid and finally with water.  Yield almost theoretical. In the above process only one-half of the amine is transformed into its benzoyl derivative. By working in presence of dilute sodium hydroxide aniline is completely converted into its benzoyl derivative.

Preparation of benzanilide

Preparation of benzanilide

A mixture of 15 g of aniline, and 20 g of benzoic acid is heated to 180° C. The temperature raised gradually to 225° C; a further 10 g of aniline are added, and heating continued. The hot mass is then poured into an evaporating dish and allowed to solidify. It is powdered, washed with dilute hydrochloric acid to remove unchanged base, then with water to remove the benzoate, then with dilute caustic soda to remove free acid, and finally with water. It is dried and crystallised from alcohol. Yield 80% colourless plates; insoluble, in water ; m.p. 162° C.

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

IUPAC Name

N-phenylbenzamide

InChI

InChI=1S/C13H11NO/c15-13(11-7-3-1-4-8-11)14-12-9-5-2-6-10-12/h1-10H,(H,14,15)

InChI Key

ZVSKZLHKADLHSD-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(=O)NC2=CC=CC=C2

MeSH Synonyms

benzanilide

Depositor-Supplied Synonyms

N-Phenylbenzamide, BENZANILIDE, 93-98-1, N-Phenyl-benzamide, N-Benzoylaniline, Benzamide, N-phenyl-, Benzoic acid anilide, ZVSKZLHKADLHSD-UHFFFAOYSA-N, phenyl-N-benzamide, AE-641/31373004, N-benzoylphenylamine, ACMC-209roi, N-Phenylbenzoic acid amide, AC1L1O5V, TimTec1_003094, SCHEMBL31966, KSC487E0R, UNII-AK1B12366O, 108227_ALDRICH, 442470_SUPELCO, ARONIS003508, CHEMBL115523, SCHEMBL8861823, 12081_FLUKA, CTK3I7208, NSC3131, MolPort-000-564-109, AK1B12366O, HMS1542M14, ZINC142820, NSC 3131, NSC-3131, EINECS 202-292-7, ANW-40144, CCG-40583, SBB058065, STK036609, ZINC00142820, AKOS000492910, MCULE-2801857425, RTR-031111, AC-21003, AJ-12476, AK116692, AN-24277, BC218557, KB-74972, OR020059, OR192899, OR378651, ST040200, ZB004944, AI3-01046, DB-013672, TR-031111, B0016, FT-0622634, ST24031434, X4220, SR-01000630713-1, BRD-K72443974-001-01-0, 3B3-033046, 100747-15-7

Removed Synonyms

CID7168

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *