2-Aminobenzonitrile → diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzylphosphonate

HRID 54898

Reaction equation

HRID 54898 reaction equation
[C:1](#[N:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:10]([O:12][P:13]([CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O:15][CH2:16][CH3:17])=[O:14])[CH3:11]>N1C=CC=CC=1.ClCCl>[C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:23]([C:22]1[CH:26]=[CH:27][C:19]([CH2:18][P:13](=[O:14])([O:12][CH2:10][CH3:11])[O:15][CH2:16][CH3:17])=[CH:20][CH:21]=1)=[O:24])#[N:9]

Participants

5

Reactant 2

HCID 729132-AminobenzonitrileHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chloride

Product 1

HCID 10738021diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzylphosphonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 15.7 g portion of anthranilonitrile was dissolved in 50 ml of pyridine. While the solution was stirred under ice-cooling, a solution of 40.7 g of 4-[(diethoxyphosphoryl)-methyl]benzoyl chloride in 50 ml of dry dichloromethane was added dropwise. The stirring was continued at room temperature for 12 hours, after which the reaction mixture was diluted with 200 ml of dichloromethane and washed with diluted hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from chloroform-n-hexane to provide 25.9 g of diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzyl-phosphonate as colorless crystals.

Workup

  1. temperaturecooling
  2. washwashed with diluted hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from chloroform-n-hexane

Sources & evidence

ORD record
ord-607114bdcd884d68b566960c08712939
Source dataset
uspto-grants-1997_04
Patent number
US05624918

Linked notes

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