Synthesis of benzamide (benzoic acid amide; benzoylamide)

Preparation of benzamide

Preparation of benzamide by hydrolyzing benzonitrile with sulfuric acid

Preparation of benzamide by hydrolyzing benzonitrile with sulfuric acid

Preparation of benzamide by hydrolyzing benzonitrile with sulfuric acid

2 g (or 2 ml) of benzonitrile is mixed with 20 ml of 90% sulfuric acid, which is prepared by mixing 25 ml of the concentrated sulfuric acid cautiously with gentle shaking with 5 ml of water. After mixing a clear solution is rapidly obtained, which is heated under reflux for 20 minutes. When hydrolysis reaction is complete the solution is cooled and poured in to 50 g of crushed ice. The obtained precipitate of crude benzamide is filtered, washed with water, and recrystallized from hot water, yielding 1 g of final product with melting point 128-130° C.

Preparation of benzamide by oxidatizing benzonitrile with hydrogen peroxide

Preparation of benzamide by oxidatizing benzonitrile with hydrogen peroxide

Preparation of benzamide by oxidatizing benzonitrile with hydrogen peroxide

Alternatively benzamide could be prepared by mixing 3 g (or 3 ml) of benzonitrile with 50 ml of 10% hydrogen peroxide and  1 ml of 10% aqueous sodium hydroxide solution. The solution is gently warmed, with proper stirring, to 40° until the oily suspension of the benzonitrile has been completely replaced by the crystalline benzamide. When the reaction is complete, usually after 45-60 minutes, the solution is cooled, benzamide filtered, washed with water and recrystallized from hot water. The yield of benzamide is 2-2.5 g.

Practical organic chemistry, by F. G. Mann, 193-194, 1960

Preparation of benzamide

Preparation of benzamide

10 g finely powdered dry ammonium bicarbonate are placed in a mortar in a fume cupboard. 5 g benzoyl chloride are added and the whole well mixed with a pestle during 10 minutes. If the odour of benzoyl chloride persists at the end of this time, a few drops of conc. ammonia are added. The product is diluted with water, the benzamide filtered off and recrystallised from boiling water. Yield 93%, glistening plates; m.p. 130° C.

Systematic organic chemistry, by W. M. Cumming, 301, 1937.

IUPAC Name

benzamide

InChI

InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)

InChI Key

KXDAEFPNCMNJSK-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(=O)N

MeSH Synonyms

benzamide

Depositor-Supplied Synonyms

Benzamide, Benzoic acid amide, Benzoylamide, 55-21-0, Phenylcarboxyamide, Phenylcarboxamide, Benzenecarboxamide, Amid kyseliny benzoove, Phenyl Carboxyamide, Amid kyseliny benzoove [Czech], BENZOIC ACID,AMIDE, CCRIS 4594, CHEMBL267373, CHEBI:28179, HSDB 6360, KXDAEFPNCMNJSK-UHFFFAOYSA-N, NSC 3114, EINECS 200-227-7, SBB058198, UNII-6X80438640, BRN 0385876, AI3-01031, 27208-38-4, N-benzoylamine, benzoyl nitrogen, Phenyl carboxamide, benzene carboxamide, AC1L1DFU, WLN: ZVR, benzene carboximidoic acid, PhC(O)NH2, Lopac-B-2009, ACMC-1AZ9T, DSSTox_CID_1709, bmse000668, PhC(=O)NH2, DSSTox_RID_76288, DSSTox_GSID_21709, Lopac0_000160, SCHEMBL16352, benzamide (ACD/Name 4.0), KSC175C0F, MLS000069472, 135828_ALDRICH, 150762_ALDRICH, 399337_ALDRICH, ARONIS003511, HMDB04461, NSC3114, MolPort-001-497-861, YSKVTRZUSMWAQJ-UHFFFAOYSA-N, HMS2231M11, HMS3260O22, HMS3371I16, NSC-3114, Tox21_200621, ANW-32259, STK069333, ZINC00152996, AKOS000118773, CCG-204255, LP00160, LS-1353, MCULE-2811211507, RP19412, RTC-010676, CAS-55-21-0, NCGC00015142-01, NCGC00015142-02, NCGC00015142-03, NCGC00015142-04, NCGC00015142-05, NCGC00015142-06, NCGC00091355-01, NCGC00091355-02, NCGC00091355-03, NCGC00258175-01, 4CN-0762, AJ-12870, AK-77684, AN-24423, BP-21224, CJ-01214, KB-47506, SMR000059089, ZB005314, ST2412632, B0012, B0220, B1418, EU-0100160, FT-0622630, FT-0622631, ST45040306, AZ0001-0025, B 2009, C09815, M-4040, 12078-EP2272827A1, 12078-EP2275469A1, 12078-EP2284157A1, 12078-EP2284169A1, 12078-EP2287161A1, 12078-EP2287162A1, 12078-EP2287940A1, 12078-EP2289894A2, 12078-EP2289965A1, 12078-EP2292593A2, 12078-EP2295061A1, 12078-EP2295402A2, 12078-EP2295413A1, 12078-EP2295421A1, 12078-EP2295424A1, 12078-EP2295550A2, 12078-EP2298076A1, 12078-EP2298077A1, 12078-EP2298731A1, 12078-EP2298828A1, 12078-EP2300455A2, 12078-EP2301353A1, 12078-EP2301929A1, 12078-EP2301935A1, 12078-EP2301983A1, 12078-EP2305031A1, 12078-EP2305034A1, 12078-EP2305035A1, 12078-EP2305662A1, 12078-EP2305674A1, 12078-EP2305687A1, 12078-EP2308848A1, 12078-EP2308858A1, 12078-EP2311494A1, 12078-EP2314583A1, 12078-EP2314585A1, 12078-EP2316825A1, 12078-EP2316831A1, 12078-EP2371810A1, 74166-EP2308857A1, 4-09-00-00725 (Beilstein Handbook Reference), A830526, 3B4-1070, I01-6590, 6X80438640, InChI=1/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9

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2 comments

  1. RAJAT KAUSHIK

    SITE SEEMS REALLY HELPFUL. THE PHRASES OR WORDS MIGHT HELP YOU A BIT IN UNDERSTANDING THE CHEMISTRY OF COMPOUNDS,THEIR SYNTHESIS AND MECHANISM OF ACTION

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