Synthesis of acetanilide

Preparation of acetanilide

Preparation of acetanilide

Preparation of acetanilide

100 g aniline and 150 g acetic acid are mixed in a round flask of one-litre capacity, fitted with an air-condenser, and boiled 10 to 12 hours. The tube forming the air-condenser should not be too long, in order that the water vapor may escape while the aniline and acetic acid are condensed. The hot reaction mixture is poured into hot water containing 30 g of concentrated hydrochloric acid. After cooling, the crude acetanilide is filtered washed with distilled water. The filtrate contains about 20-30 grams of aniline hydrochloride, which, could be regenerated. The acetanilide is dried at 110-120° C. The yield of acetanilide is 220-250 g. Acetanilide is purified by crystallization from hoe water forms white leafy crystals melting at 115° C, boiling at 295° C. By boiling with concentrated hydrochloric acid, acetanilide is hydrolyzed to aniline and acetic acid.

Hydrolysis of acetanilide

Hydrolysis of acetanilide

The Synthetic Dyestuffs and the Intermediate Products from which They are Derived, by J. C. Cain, 201, 1905

IUPAC Name

N-phenylacetamide

InChI

InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)

InChI Key

FZERHIULMFGESH-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NC1=CC=CC=C1

MeSH Synonyms

acetanilid, acetanilide

Depositor-Supplied Synonyms

acetanilide, N-Phenylacetamide, 103-84-4, Acetanil, Acetanilid, Antifebrin, Acetamidobenzene, Acetylaniline, Acetamide, N-phenyl-, Acetic acid anilide, N-Acetylaniline, Acetoanilide, Acetylaminobenzene, Phenalgene, Phenalgin, Aniline, N-acetyl-, N-acetylarylamine, Benzenamine, N-acetyl-, USAF EK-3, Ethananilide, n-phenylacetamid, NSC 7636, AN [Analgesic], N-Acetylaminobenzene, Caswell No. 003E, UNII-SP86R356CC, Acetic acid amide, N-phenyl-, CCRIS 4452, CHEBI:28884, HSDB 2665, NSC7636, FZERHIULMFGESH-UHFFFAOYSA-N, EINECS 203-150-7, NCGC00091326-01, AI3-01045, DSSTox_CID_2543, DSSTox_RID_76620, DSSTox_GSID_22543, AH-034/32461060, Acetamide, N-(phenyl-d5)-, 55576-55-1, CAS-103-84-4, SMR001306799, Acetamide, N-(phenyl-2,3,4,5,6-d5)-, N-phenylethanamide, N-phenyl acetamide, Spectrum_000178, AC1L1AAE, Spectrum2_001434, Spectrum3_000935, Spectrum4_001034, Spectrum5_000989, C8H9NO, WLN: 1VMR, ACMC-1AR90, Ethanimidic acid, N-phenyl-, SCHEMBL24681, KBioGR_001587, KBioSS_000658, KSC492K1L, MLS002207284, MLS002415707, DivK1c_000073, SPECTRUM1501173, SPBio_001568, 112933_ALDRICH, 397229_ALDRICH, 397237_ALDRICH, AC1Q5N69, ARONIS003513, CHEMBL269644, SP86R356CC, SCHEMBL14255226, 00400_FLUKA, 00401_FLUKA, CTK3B8627, CTK3J2515, HMDB01250, HMS500D15, KBio1_000073, KBio2_000658, KBio2_003226, KBio2_005794, KBio3_001970, MolPort-000-564-428, NINDS_000073, ACETIC ACID,AMIDE,N-PHENYL, BCPP000440, HMS1921N07, HMS2092J11, HMS2234E18, HMS3374L04, Pharmakon1600-01501173, 112933_SIAL, NSC-7636, Tox21_111113, Tox21_200925, ANW-74570, AR-1K8037, CCG-38984, LS-366, NSC757879, SBB040833, STK046402, ZINC00142824, AKOS000121114, Tox21_111113_1, BCP9000226, MCULE-1268638727, NE10600, NSC-757879, RTR-000889, IDI1_000073, NCGC00091326-02, NCGC00091326-03, NCGC00091326-04, NCGC00091326-06, NCGC00258479-01, AJ-12477, AK-44452, AN-24658, CJ-01073, I054, ST040202, ZB004945, AB2000635, KB-259064, KB-294800, ST2419721, TR-000889, 795-EP2269979A1, 795-EP2277880A1, 795-EP2288595A2, 795-EP2292610A1, 795-EP2296664A1, 795-EP2298729A1, 795-EP2308872A1, 795-EP2316829A1, FT-0621730, FT-0621731, FT-0661047, 1947-EP2275407A1, 1947-EP2298752A1, 1947-EP2301918A1, C07565, 3B4-1481, I01-2061, InChI=1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10, N-phenylacetamide;Acetanil;Acetamidobenzene;Acetylaniline;NSC 7636;Antifebrin, 88070-49-9

Removed Synonyms

Anilide, N-Phenyl-acetamide, 2-Acetanilide, 2-PHENYLACETAMIDE, CID904, c0657, A1882, C508827, 103-81-1, AN, 15826-91-2, 61377-32-0, ACN

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