Acetyl chloride → N-(3-fluoro-2-methylphenyl)acetamide

HRID 1865159Notes

Reaction equation

HRID 1865159 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8].C(N(CC)CC)C>C(Cl)Cl>[C:1]([NH:8][C:7]1[CH:9]=[CH:10][CH:11]=[C:12]([F:13])[C:6]=1[CH3:5])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 2855533-Fluoro-2-methylaniline

Product 1

HCID 1489284N-(3-fluoro-2-methylphenyl)acetamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.98 ml (27.78 mmol) of acetyl chloride were added, with stirring, to a solution of 3.161 g (25.26 mmol of 2-methyl-3-fluoroaniline and 3.87 ml (27.78 mmol) of triethylamine in 50 ml of DCM at 0° C. The solution was allowed to warm up to ambient temperature and was stirred for 1 hour. The solution was washed with water (3 times 50 ml), the product was dried with MgSO4 and the solvent was removed under reduced pressure. After recrystallization from a mixture of mineral oil/ethyl acetate (EtOac), 3.844 g (91%) of the title compound were obtained in the form of white crystals.

Workup

  1. washThe solution was washed with water (3 times 50 ml)
  2. dry with materialthe product was dried with MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customAfter recrystallization
  5. additionfrom a mixture of mineral oil/ethyl acetate (EtOac)

Sources & evidence

ORD record
ord-7b73f3638bf74eaf87933dcd38da0fdb
Source dataset
uspto-grants-2009_12
Patent number
US07626018B2

Reaction notes

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