Pyridine → N-(4-Iodophenyl)acetamide

HRID 8388

Reaction equation

HRID 8388 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].N1C=CC=CC=1>C(OCC)(=O)C>[CH3:10][C:9]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 108934-Iodoaniline

Product 1

HCID 12147N-(4-Iodophenyl)acetamideYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Iodoaniline (11.0 g, 50.4 mmol) was dissolved in 60 mL of ethyl acetate and the solution was added with 10 mL of acetic anhydride (10.8 g, 106 mmol) and 7.8 mL of pyridine (7.65 g, 99.4 mmol), and the mixture was stirred at room temperature for 2 hours with an equipment of a CaCl2 tube. A solvent was evaporated under reduced pressure to obtain 4-iodoacetanilide (yield: 13.0 g, percent yield: 99.0%).

Workup

  1. customA solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f23b6d9e5abd4f8d9c2f50a4359ddf11
Source dataset
uspto-grants-2006_08
Patent number
US07087766B2

Linked notes

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