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

HRID 2079449Notes

Reaction equation

HRID 2079449 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-e222f1b295ed46d6b3e078b408b00ad9
Source dataset
uspto-grants-2011_04
Patent number
US07932050B2

Reaction notes

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