Aniline → N-phenyl-4-cyano-2,6-dinitroaniline

HRID 644555Notes

Reaction equation

HRID 644555 reaction equation
Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[C:17]1([NH:16][C:2]2[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 160084-Chloro-3,5-dinitrobenzonitrile

Product 1

HCID 85829898N-phenyl-4-cyano-2,6-dinitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (5° C.) solution of 4-chloro-3,5-dinitrobenzonitril (50 g, 0.22 mol) in anhydrous DMF (200 ml) was added aniline (40 ml, 0.44 mol) dropwise over 1 hour. The resultant mixture was stirred for additionally 1 hour at 0° C. and then poured into ice-water (1400 g). The precipitate was filtered off, washed with water and air-dried to afford N-phenyl-4-cyano-2,6-dinitroaniline, quantitatively.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customair-dried

Sources & evidence

ORD record
ord-d01be521c76347ef8edd935d0e5df0d6
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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