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Water → 2-(Methylamino)-6-(phenoxyacetylamino)benzonitrile

HRID 2248753
Notes
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Reaction equation

HRID 2248753 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.[O:18]([CH2:25][C:26](Cl)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C(Cl)Cl>[CH3:11][NH:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([NH:1][C:26](=[O:27])[CH2:25][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:3]=1[C:4]#[N:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 69703Phenoxyacetyl chlorideHCID 127157172-Amino-6-(methylamino)benzonitrile

Product 1

HCID 149862632-(Methylamino)-6-(phenoxyacetylamino)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

To a solution of 2-amino-6-(methylamino)benzonitrile (3.3 g) in methylene chloride (50 ml) is added pyridine (3.6 ml), and thereto is added dropwise phenoxyacetyl chloride (6.2 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 ethanol to give the title compound (1.4 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 ethanol

Sources & evidence

ORD record
ord-64a025258a8842658de7db8e85efeeef
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