Acetic Anhydride → N-(3,4-Difluorophenyl)acetamide

HRID 720506Notes

Reaction equation

HRID 720506 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C(N(CC)CC)C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:17](=[O:19])[CH3:18])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 774693,4-Difluoroaniline

Product 1

HCID 223109N-(3,4-Difluorophenyl)acetamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,4-difluoroaniline (50 ml; 0.5 mole) and triethylamine (70 ml; 0.5 mol) in dichloromethane (1.51) is cooled down using an ice bath. Acetic anhydride (71.5 ml; 0.75 mol) is added dropwise and the reaction mixture is then agitated for 1 hour at ambient temperatue. The mixture obtained is then washed successively with water, a 10% solution of sodium bicarbonate and saturated salt water. The organic fraction is dried over sodium sulphate and concentrated under reduced pressure. The residue is suspended in pentane, filtered and dried under reduced pressure in order to produce the product in the title (78 g; 91% yield) in the form of a whitish solid (M.p. 126–127.5° C.).

Workup

  1. temperatureis cooled down
  2. customThe mixture obtained
  3. washis then washed successively with water
  4. dry with materialThe organic fraction is dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. filtrationfiltered
  7. customdried under reduced pressure in order

Sources & evidence

ORD record
ord-50b025d2a185464181f1cf937d520f2e
Source dataset
uspto-grants-2006_11
Patent number
US07135478B2

Reaction notes

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