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

HRID 2248752Notes

Reaction equation

HRID 2248752 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][CH3:12])[C:3]=1[C:4]#[N:5].N1C=CC=CC=1.[CH2:19]([O:21][CH2:22][C:23](Cl)=[O:24])[CH3:20].O>C(Cl)Cl>[CH2:19]([O:21][CH2:22][C:23]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][CH3:12])[C:3]=1[C:4]#[N:5])=[O:24])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 84189Ethoxyacetyl chlorideHCID 127157182-Amino-6-(ethylamino)benzonitrile

Product 1

HCID 149862622-(Ethoxyacetylamino)-6-(ethylamino)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-6-(ethylamino)benzonitrile (4 g) in methylene chloride (100 ml) is added pyridine (2.8 ml), and thereto is added dropwise ethoxyacetyl chloride (3.9 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 (4.1 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
  5. customThe resulting crude crystals are recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a84c8372494343af8baf0767e66df4e3
Source dataset
uspto-grants-1991_08
Patent number
US05041462

Reaction notes

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