Synthesis of 4-iodoacetanilide

Preparation of 4-iodoacetanilide

Preparation of 4-iodoacetanilide

Preparation of 4-iodoacetanilide

A solution of 1 mole of iodine monochloride is dropped, with stirring, into a solution of 1 mole of acetanilide in 150 ml of glacial acetic acid (exothermic reaction!) and the reaction mixture is stirred for a further few hours yielding precipitates of 4-iodoacetanilide. After 12 hours, the mixture is poured into 2 liters of water, and the product is collected and washed with water and dilute sodium hydroxide solution. Recrystallization of this crude material from ethanol gives a 90% yield of the 4-iodoacetanilide, m.p. 184° C.

Ber. Deut. Chem. Ges., 11, 108, (1878).
J. Chem. Soc, 95, 124, (1914).

IUPAC Name

N-(4-iodophenyl)acetamide

InChI

InChI=1S/C8H8INO/c1-6(11)10-8-4-2-7(9)3-5-8/h2-5H,1H3,(H,10,11)

InChI Key

SIULLDWIXYYVCU-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NC1=CC=C(C=C1)I

MeSH Synonyms

4-iodoacetanilide, p-iodoacetanilide, para-iodoacetanilide

Depositor-Supplied Synonyms

N-(4-Iodophenyl)acetamide, 4-Iodoacetanilide, 622-50-4, p-Iodoacetanilide, 4′-Iodoacetanilide, Acetamide, N-(4-iodophenyl)-, ACETANILIDE, 4′-IODO-, SIULLDWIXYYVCU-UHFFFAOYSA-N, NSC 2161, BRN 2085726, AI3-23888, ST50556296, 4′-Iodo-acetanilide, PubChem3293, ACMC-20akb8, AC1Q1KUW, Maybridge1_006480, para-acetamino-iodo-benzene, WLN: IR DMV1, AC1L1YY9, N-(4-iodophenyl) acetamide, N-(4-iodophenyl)-acetamide, 4-(N-acetylamino)iodobenzene, Acetamide,N-(4-iodophenyl)-, AKOS AKM01244, N-(4-iodo-phenyl)-acetamide, SCHEMBL669782, CTK5B4831, HMS559O12, ZINC78961, NSC2161, MolPort-000-396-056, NSC-2161, CCG-56184, CI-274, KM0594, ZINC00078961, AKOS002813447, AS02201, MCULE-2439343180, TRA-0184327, AJ-10468, AK115722, AN-46735, KB-55941, LS-10777, OR013843, OR105957, ZB002815, TC-165995, AM20040882, FT-0618774, I0846, 1Y-0922, 4-12-00-01546 (Beilstein Handbook Reference), AH-034/05420003, I01-5906, SR-01000645158-1, 3B3-052921

Removed Synonyms

N- acetamide, CID12147

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