Acetoxyacetyl chloride → Acreozast

HRID 1165885Notes

Reaction equation

HRID 1165885 reaction equation
[Cl:1][C:2]1[C:9]([NH2:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH2:11].[C:12]([O:15][CH2:16][C:17](Cl)=[O:18])(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([O:15][CH2:16][C:17]([NH:11][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([NH:10][C:17](=[O:18])[CH2:16][O:15][C:12](=[O:14])[CH3:13])[C:2]=1[Cl:1])[C:6]#[N:7])=[O:18])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 124029953,5-Diamino-4-chlorobenzonitrile

Product 1

HCID 129991Acreozast

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-chloro-3,5-diaminobenzonitrile (6.7 g) in pyridine (150 ml) is added dropwise acetoxyacetyl chloride (9.5 ml) at room temperature. The mixture is stirred at room temperature for 3 hours, and thereafter, pyridine is distilled off under reduced pressure. To the residue is added water, and the resulting solid substance is separated by filtration and dissolved in chloroform, and the insoluble substance is filtered off. The filtrate is washed with water and then with aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove the solvent. The resulting solid substance is recrystallized from ethanol to give the title compound (4.3 g) having the following physical properties.

Workup

  1. distillationpyridine is distilled off under reduced pressure
  2. additionTo the residue is added water
  3. customthe resulting solid substance is separated by filtration
  4. dissolutiondissolved in chloroform
  5. filtrationthe insoluble substance is filtered off
  6. washThe filtrate is washed with water
  7. dry with materialwith aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe resulting solid substance is recrystallized from ethanol

Sources & evidence

ORD record
ord-7d253d844eae4daaa68cb9c56f59a741
Source dataset
uspto-grants-1990_03
Patent number
US04912135

Reaction notes

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