Acetic Anhydride → N-(4-Iodophenyl)acetamide

HRID 1242262Notes

Reaction equation

HRID 1242262 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]>C(Cl)Cl>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 108934-Iodoaniline

Product 1

HCID 12147N-(4-Iodophenyl)acetamideYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-iodoaniline (20.00 g, 90.0 mmol, 1.0 equiv) triethylamine (38.4 ml, 274 mmol, 3.0 equiv) and CH2Cl2 (200 ml) was cooled to 0° C. Acetic anhydride (26.0 ml, 270 mmol, 3.0 equiv) was added drop wise. The reaction mixture was stirred at 0° C. for 10 min, and at rt for 2 h. The volatile materials were removed under vacuum, and the solid residue was dissolved in 30 ml of hot CH2Cl2. The solution was left to stand in a freezer for 72 h. The separated solid was filtered out and dried under vacuum to give N-(4-iodophenyl)acetamide (20.35 g, 86.6%). 1H NMR (CDCl3) δ 7.58–7.28 (d, 2H), 7.25–7.23 (d, 2H), 2.15 (s, 3H).

Workup

  1. waitat rt for 2 h
  2. customThe volatile materials were removed under vacuum
  3. dissolutionthe solid residue was dissolved in 30 ml of hot CH2Cl2
  4. waitThe solution was left
  5. waitto stand in a freezer for 72 h
  6. filtrationThe separated solid was filtered out
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0d84cc2fdd584470bb0ea7c9e61f42e4
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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