Acetoxyacetyl chloride → HCID 14986274, compound

HRID 2248767Notes

Reaction equation

HRID 2248767 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:3]=1[C:4]#[N:5].[C:16]([O:19][CH2:20][C:21](Cl)=[O:22])(=[O:18])[CH3:17]>N1C=CC=CC=1>[C:16]([O:19][CH2:20][C:21]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[C:3]=1[C:4]#[N:5])=[O:22])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 127157272-Amino-6-(morpholin-4-yl)benzonitrile

Product 1

HCID 14986274HCID 14986274, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-6-morpholinobenzonitrile (5.6 g) in pyridine (15 ml) is added dropwise acetoxyacetyl chloride (3.3 ml) which is cooled in an ice bath. The mixture is stirred at room temperature for 1 hour, and thereafter, pyridine is distilled off under reduced pressure and thereto is added water, and the mixture is extracted with methylene chloride. The organic layer is dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The resulting residue is recrystallized from ethanol-toluene-water to give the title compound (4.7 g) having the following physical properties.

Workup

  1. temperatureis cooled in an ice bath
  2. distillationpyridine is distilled off under reduced pressure
  3. additionis added water
  4. extractionthe mixture is extracted with methylene chloride
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe resulting residue is recrystallized from ethanol-toluene-water

Sources & evidence

ORD record
ord-7024412e01ec476590fadfcc745be884
Source dataset
uspto-grants-1991_08
Patent number
US05041462

Reaction notes

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