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

HRID 1018788Notes

Reaction equation

HRID 1018788 reaction equation
[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]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 44163954-Amino-3-iodobenzonitrile

Product 1

HCID 22991943N-(4-cyano-2-iodophenyl)acetamideYield 95%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

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).

Workup

  1. temperaturewas heated at 700
  2. temperatureunder reflux for 10 minutes (the mixture
  3. stirringstirred for 5 minutes
  4. customto give a white solid which
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-2b2caf05ec204e249163895b844ccc2a
Source dataset
uspto-grants-2002_11
Patent number
US06482982B1

Reaction notes

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