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Water → HCID 14986258, compound

HRID 2248748
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Reaction equation

HRID 2248748 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.[CH3:19][O:20][CH2:21][C:22](Cl)=[O:23].O>C(Cl)Cl>[CH2:11]([NH:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([NH:1][C:22](=[O:23])[CH2:21][O:20][CH3:19])[C:3]=1[C:4]#[N:5])[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 127157182-Amino-6-(ethylamino)benzonitrile

Product 1

HCID 14986258HCID 14986258, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-6-(ethylamino)benzonitrile (3.4 g) in methylene chloride (50 ml) is added pyridine (2.4 ml), and thereto is added dropwise methoxyacetyl chloride (2.8 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
  5. customThe resulting crude crystals are recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-18b3b16242f14763a911f42e841dd28e
Source dataset
uspto-grants-1991_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05041462

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes