Reaction #55959

ord-a9221bcf0bbb4c9692966241d39232ec

Reaction equation

CCN(CC)c1ccc(N=Nc2c(Br)cc([N+](=O)[O-])cc2[N+](=O)[O-])c(NC(C)=O)c1
2-Bromo-4,6-dinitro-2'-acetylamino-4'-(N,N-diethylamino)azobenzene
CC(=O)[O-].[Na+]
sodium acetate
NC=O
formamide
CC(=O)OC(C)=O
acetic anhydride
→
CCN(CC)c1ccc(N=Nc2c(C#N)cc([N+](=O)[O-])cc2[N+](=O)[O-])c(NC(C)=O)c1
2-Cyano-4,6-dinitro-2'-acetylamino-4'-(N,N-diethylamino)azobenzene
Yield 96.0%

Reactants

CCN(CC)c1ccc(N=Nc2c(Br)cc([N+](=O)[O-])cc2[N+](=O)[O-])c(NC(C)=O)c1
2-Bromo-4,6-dinitro-2'-acetylamino-4'-(N,N-diethylamino)azobenzene
CC(=O)[O-].[Na+]
sodium acetate
NC=O
formamide
CC(=O)OC(C)=O
acetic anhydride
—
petroleum-ether

Reagents

[Cl][Cu][Cl]
copper (II) chloride

Solvents

CCCCOC(C)=O
n-butyl acetate

Conditions

Temperature
110°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureheated
  2. 2
    TemperatureThe temperature is maintained for 5 hours after which time the reaction
  3. 3
    TemperatureThe mixture is cooled to room temperature
  4. 4
    OtherThe precipitate is collected
  5. 5
    Washwashed with petroleum-ether (100 parts)
  6. 6
    Otherdried

Procedure

2-Bromo-4,6-dinitro-2'-acetylamino-4'-(N,N-diethylamino)azobenzene (2.4 parts), copper (II) chloride (0.67 parts), anhydrous sodium acetate (1.2 parts), formamide (1.8 parts), acetic anhydride (2.0 parts) and n-butyl acetate (44 parts) are mixed together and heated, with stirring, to 110° C. during 15 minutes. The temperature is maintained for 5 hours after which time the reaction is complete. The mixture is cooled to room temperature and poured into petroleum-ether (boiling range 60-80°) (400 parts). The precipitate is collected, washed with petroleum-ether (100 parts) and dried. 2-Cyano-4,6-dinitro-2'-acetylamino-4'-(N,N-diethylamino)azobenzene is obtained in 96% yield.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04222935uspto-grants-1980_09