Acetic Anhydride → N-(4-Iodophenyl)acetamide

HRID 1281990Notes

Reaction equation

HRID 1281990 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)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-Iodo-aniline (15 g, 69 mmol) in dry CH2Cl2 (100 ml) was added acetic anhydride(14.09 g, 138 mmol) at room temperature, the reaction mixture was then stirred for 2 hr. The gray color precipitate formed during the reaction was filtered, washed with ether and collected, the mother solution was concentrated to dryness and AcOEt was added, the resulting precipitate was filtered, washed with ether and combined with the previous solid as the desired product (15.95 g, 88.7%).

Workup

  1. customThe gray color precipitate
  2. customformed during the reaction
  3. filtrationwas filtered
  4. washwashed with ether
  5. customcollected
  6. concentrationthe mother solution was concentrated to dryness and AcOEt
  7. additionwas added
  8. filtrationthe resulting precipitate was filtered
  9. washwashed with ether

Sources & evidence

ORD record
ord-f662b6dea67d44c4b4fd904b89edf336
Source dataset
uspto-grants-2002_09
Patent number
US06455545B2

Reaction notes

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