Acetic Anhydride → N-(4-cyano-2-iodophenyl)acetamide

Reaktionsgleichung

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[I:10].[C:11](OC(=O)C)(=[O:13])[CH3:12]>S(=O)(=O)(O)O.O>[C:11]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[I:10])(=[O:13])[CH3:12]

Komponenten

Versuchsvorschrift

A mixture of 8.54 g (0.035 mole) of 4-amino-3-iodobenzonitrile (31), 16 mL (16.32 g, 0.16 mole) of acetic anhydride and five drops of concentrated sulfuric acid was heated at 700 under reflux for 10 minutes (the mixture became thick when the temperature reached 400 and some manual stirring was required). The reaction mixture was poured over 400 mL of cold water and stirred for 5 minutes to give a white solid which was filtered and dried, yielding 9.48 g (95%) of 32 as white powder, mp 176-181°. Infrared (IR) and NMR analysis gave the following results: IR (potassium bromide): 3276 (NH), 2230 (CN), 1663 (C=O), 1517, 1297 cm−1. 1H nmr (90 MHz, CDCI3):δ 8.73 (1H, br s, NH), 8.13-8.05 (2H, m, H-5 and H-2), 7.65 (1 H; dd, 3JH5-H6=8.4 Hz, 4JH2-H6=1.8 Hz; H-6), 2.25 (3H, s, CH3).