Water → 2-(Ethoxyacetylamino)-6-(methylamino)benzonitrile

HRID 2248751Notes

Reaction equation

HRID 2248751 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH3:11])[C:3]=1[C:4]#[N:5].N1C=CC=CC=1.[CH2:18]([O:20][CH2:21][C:22](Cl)=[O:23])[CH3:19].O>C(Cl)Cl>[CH2:18]([O:20][CH2:21][C:22]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH3:11])[C:3]=1[C:4]#[N:5])=[O:23])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 84189Ethoxyacetyl chlorideHCID 127157172-Amino-6-(methylamino)benzonitrile

Product 1

HCID 149862612-(Ethoxyacetylamino)-6-(methylamino)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-6-(methylamino)benzonitrile (3.3 g) in methylene chloride (50 ml) is added pyridine (3.9 ml), and thereto is added dropwise ethoxyacetyl chloride (5 ml) which is cooled in an ice bath. The mixture is stirred at room temperature for 1 hour, and thereafter, water is added thereto, 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 crude crystals are recrystallized from ethyl acetate-hexane to give the title compound (3.2 g) having the following physical properties.

Workup

  1. temperatureis cooled in an ice bath
  2. extractionthe mixture is extracted with methylene chloride
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. distillationthe solvent is distilled off under reduced pressure The resulting crude crystals
  5. customare recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-444b27a8709145919be95f4c2e62fd23
Source dataset
uspto-grants-1991_08
Patent number
US05041462

Reaction notes

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