Acetic Anhydride → N-(4-Fluoro-2-methylphenyl)acetamide

HRID 17546

Reaction equation

HRID 17546 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1>C(Cl)(Cl)Cl>[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:5](=[O:7])[CH3:6])=[C:11]([CH3:16])[CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 679824-Fluoro-2-methylaniline

Product 1

HCID 2737623N-(4-Fluoro-2-methylphenyl)acetamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acetic anhydride (17.7 ml, 0.19 mol) was dropwise added to 4-fluoro-2-methylaniline (234 g, 0.19 mol). The solidified reaction mixture was dissolved in chloroform, washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, then dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the residue was dried with a vacuum pump to obtain the entitled compound (31.7 g, 99%) as a pale red solid.

Workup

  1. customThe solidified reaction mixture
  2. washwashed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated away under reduced pressure
  5. customthe residue was dried with a vacuum pump

Sources & evidence

ORD record
ord-b28a3fb55f434213817c419a6f86b40a
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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