Acetyl chloride → N-(5-Acetyl-2-fluorophenyl)acetamide

HRID 75955Notes

Reaction equation

HRID 75955 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([NH2:11])[CH:5]=1)=[O:3].[C:12](Cl)(=[O:14])[CH3:13].CCN(C(C)C)C(C)C>CN(C=O)C>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 106069533'-Amino-4'-fluoroacetophenone

Product 1

HCID 53431926N-(5-Acetyl-2-fluorophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a round, bottom flask was added 3-amino-4-fluoroacetophenone (Method 64, 1 g, 6.54 mmol) in DMF (15 ml), followed by the addition of acetyl chloride (0.56 ml, 7.84 mmol) and DIEA (2.3 ml, 13.08 mmol). The solution was set to stir at room temperature. The reaction appeared complete by TLC after 30 min. The reaction was then quenched with water and partitioned with EtOAc. The layers were cut, followed by an additional wash of the aqueous with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude residue obtained (1.17 g), was used directly in the next step. 1H NMR (CDCl3) δ 8.94 (d, J=7.54 Hz, 1H) 7.71 (d, 1H) 7.43 (s, 1H) 7.15 (s, 1H) 2.56-2.60 (m, 3H) 2.21-2.28 (m, 3H).

Workup

  1. customThe reaction was then quenched with water
  2. custompartitioned with EtOAc
  3. washan additional wash of the aqueous with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab74ac6029bf48b7af758aee89231fad
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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