4-Nitrobenzaldehyde → 2-(4-Nitrobenzylidene)amino-3,3-dichloropropenonitrile

HRID 1060506Notes

Reaction equation

HRID 1060506 reaction equation
[NH2:1][C:2](=[C:5]([Cl:7])[Cl:6])[C:3]#[N:4].[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)([O-:10])=[O:9]>C1(C)C=CC=CC=1>[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[N:1][C:2](=[C:5]([Cl:7])[Cl:6])[C:3]#[N:4])=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 122571202-Amino-3,3-dichloroprop-2-enenitrile

Product 1

HCID 122907202-(4-Nitrobenzylidene)amino-3,3-dichloropropenonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-amino-3,3-dichloropropenonitrile (15.0 g, 0.11 mole) and 4-nitrobenzaldehyde (15.1 g, 0.10 mmol) in toluene (200 ml) was refluxed for 23 hours. The mixture was evaporated, methanol (100 ml) was added and the mixture was allowed to stand overnight. After filtration, the title compound was isolated as a brown-yellow solid.

Workup

  1. customThe mixture was evaporated
  2. additionmethanol (100 ml) was added
  3. filtrationAfter filtration

Sources & evidence

ORD record
ord-d27838256c1e4ffd9ab86d04f0ff20c9
Source dataset
uspto-grants-2003_02
Patent number
US06524552B2

Reaction notes

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