Synthesis of acetamide

Preparation of acetamide

Preparation of acetamide

Preparation of acetamide

To 75 g of glacial acetic acid heated to 40-50° C 100 g of finely pulverized ammonium car­bonate is added until an alkaline pH is reached. The viscous reaction mass is warmed to 80-90° C, until acidic pH and then poured directly into wide tubes of hard glass, which have been previously warmed in a flame. The glass tube is sealed and heated for 5 hours in a furnace at 220-230° C. Then the glass tube is cooled to room temperature and crude acetamide is transferred from glass tube to the distillation flask. The reaction product is fractionated starting at 180° C, at which point the acetamide begins to distill. The fraction passing over between 180-230° C  is collected and the crystals separating out are pressed on a drying plate to remove the liquid impurities. By another distillation of the collected crystals, the almost pure acetamide boiling at 223° C passes over. The yield of acetamide is 40 grammes. To obtain very pure acetamide it is  crystallized from ether yielding colorless, odorless crystals, melting at 82° C.

The practical methods of organic chemistry, by L. Gattermann, 151-152, 1918.

Preparation of acetamide is presented in the following video by Doug’s Lab.

Preparation of acetamide from ethyl acetate and ammonia

Preparation of acetamide

Preparation of acetamide

15 g ethyl acetate are treated in a small flask with an equal weight of conc. ammonia solution. The flask is loosely corked and left in a war m place until the two layers originally present give place to one uniform solution. This solution is then distilled, water, alcohol and ammonia passing over up to 100° C; the fraction 210-225° C is separately collected, and if it does not solidify on cooling it is redistilled. The final product is recrystallised from ether. Yield 80%, m.p. 82° C.

Systematic organic chemistry, by W. M. Cumming, 300-301, 1937.

IUPAC Name

acetamide

InChI

InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)

InChI Key

DLFVBJFMPXGRIB-UHFFFAOYSA-N

Canonical SMILES

CC(=O)N

MeSH Synonyms

acetamide, acetamide, monosodium salt

Depositor-Supplied Synonyms

acetamide, Ethanamide, Acetic acid amide, 60-35-5, Methanecarboxamide, Acetimidic acid, Amide C2, Ethanimidic acid, acetamid, acetoamide, Caswell No. 003H, CCRIS 2, NCI-C02108, Amid kyseliny octove, HSDB 4006, Acetimidic acid (VAN), CH3CONH2, UNII-8XOE1JSO29, Amid kyseliny octove [Czech], AI3-02060, CHEBI:27856, DLFVBJFMPXGRIB-UHFFFAOYSA-N, EINECS 200-473-5, NSC 25945, BRN 1071207, Essigsaeureamid, Azetamid, Ethanamid, 1449-72-5, DSSTox_CID_5, Ethanimidic acid (9CI), Lopac-A-0500, ACMC-1AWJ5, bmse000825, bmse000895, AC1L18NI, AC1Q2B5A, WLN: ZV1, 8XOE1JSO29, DSSTox_RID_75317, DSSTox_GSID_20005, Lopac0_000003, KSC353G6F, MLS002153504, BIDD:ER0566, CHEMBL16081, 150703_ALDRICH, A0500_SIAL, GTPL4661, 14-Methylhexadec-9-Enoic Acid, 00160_FLUKA, 75434_FLUKA, CHEBI:49028, CTK1A5953, CTK2F3362, MolPort-001-779-697, HMS3260A07, Acetamide (6CI,7CI,8CI,9CI), NSC25945, STR01066, Tox21_300776, ANW-20374, NSC-25945, STL283915, AKOS000118788, AKOS015917387, CCG-204099, DB02736, LP00003, LS-1431, MCULE-9280264861, RL04274, RTR-037243, CAS-60-35-5, NCGC00015030-01, NCGC00015030-02, NCGC00015030-03, NCGC00015030-04, NCGC00015030-05, NCGC00093530-01, NCGC00093530-02, NCGC00254680-01, 4CN-0956, AK-97258, AN-23637, KB-47044, SMR000326670, AB1002187, ST2412615, TR-037243, A0007, A0210, EU-0100003, FT-0603458, FT-0621721, FT-0621725, FT-0625737, LT00795814, 9745-EP2269990A1, 9745-EP2275407A1, 9745-EP2275469A1, 9745-EP2287940A1, 9745-EP2289890A1, 9745-EP2289965A1, 9745-EP2295402A2, 9745-EP2295550A2, 9745-EP2298744A2, 9745-EP2298749A1, 9745-EP2298761A1, 9745-EP2298776A1, 9745-EP2298777A2, 9745-EP2298828A1, 9745-EP2301918A1, 9745-EP2301933A1, 9745-EP2301983A1, 9745-EP2305640A2, 9745-EP2305648A1, 9745-EP2305687A1, 9745-EP2308872A1, 9745-EP2308873A1, 9745-EP2308880A1, 9745-EP2311808A1, 9745-EP2311827A1, 9745-EP2311829A1, 9745-EP2311842A2, 9745-EP2314593A1, 9745-EP2316829A1, 9745-EP2316831A1, 9745-EP2316834A1, A 0500, C06244, 25464-EP2284166A1, 25464-EP2314580A1, 25704-EP2298729A1, 25704-EP2315303A1, 4-02-00-00399 (Beilstein Handbook Reference), A832706, 3B4-0692, I14-9593, S14-1087, InChI=1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4, ACETAMIDE (SEE ALSO N-(4-FLUORENYL)ACETAMIDE 28322-02-3), 02U, 27595-75-1, CNM

Removed Synonyms

Methylformamide, Ethinamide, ACETYL GROUP, 10-Methylundecanoic acid, acetamide, monosodium salt, Delta-3isotetradecenoic Acid, CID178, c0658, 3′-DEOXY-3′-ACETAMIDO-URIDINE, C030686, ACM, 536-33-4, ACE, ADU, LNG, M12

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