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

HRID 1168150Notes

Reaction equation

HRID 1168150 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 70° under reflux for 10 minutes (the mixture became thick when the temperature reached 40° 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:

Workup

  1. temperaturewas heated at 70°
  2. temperatureunder reflux for 10 minutes (the mixture
  3. customreached 40°
  4. stirringstirred for 5 minutes
  5. customto give a white solid which
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-bb6c986914f84ec58c8a84e6a0d5d17a
Source dataset
uspto-grants-2003_09
Patent number
US06624153B2

Reaction notes

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