Water → 2-(Acetoxyacetylamino)-6-chlorobenzonitrile

HRID 2248762Notes

Reaction equation

HRID 2248762 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[C:18]([O:21][CH2:22][C:23](Cl)=[O:24])(=[O:20])[CH3:19].O>C(Cl)(Cl)Cl>[C:18]([O:21][CH2:22][C:23]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]#[N:5])=[O:24])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 810562-Amino-6-chlorobenzonitrile

Product 1

HCID 149862692-(Acetoxyacetylamino)-6-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-amino-6-chlorobenzonitrile (4.6 g) in chloroform (100 ml) is added triethylamine (4.8 ml), and thereto is added dropwise acetoxyacetyl chloride (3.8 ml). The mixture is stirred at room temperature for 1 hour, and thereafter, water is added thereto, and the mixture is extracted with chloroform. The organic layer is washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The resulting crude crystals are recrystallized from ethanol-water to give the title compound (3.8 g) having the following physical properties.

Workup

  1. extractionthe mixture is extracted with chloroform
  2. washThe organic layer is washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe resulting crude crystals are recrystallized from ethanol-water

Sources & evidence

ORD record
ord-fa66a92a51c248498c18d5df20790463
Source dataset
uspto-grants-1991_08
Patent number
US05041462

Reaction notes

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