Formamide → 2-((4-(Diethylamino)phenyl)azo)-5-nitrobenzonitrile

HRID 27678

Reaction equation

HRID 27678 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[N:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][CH:14]=1.C([O-])(=O)C.[Na+].[CH:29]([NH2:31])=O.C(OC(=O)C)(=O)C>[Cu]I.C(OCCCC)(=O)C>[C:29]([C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[N:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][CH:14]=1)#[N:31]

Participants

7

Reactant 4

HCID 713FormamideHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 233414442-Bromo-4-nitro-4'-(N,N-diethylamino)azobenzene

Product 1

HCID 30158222-((4-(Diethylamino)phenyl)azo)-5-nitrobenzonitrileYield 75%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31272Butyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

2-Bromo-4-nitro-4'-(N,N-diethylamino)azobenzene (1.9 parts), copper (I) iodide (0.95 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 temperatures is maintained at 110° C. for 31/2 hours when reaction is adjudged complete by thin layer chromatography. The solvent is removed at 80° C. under reduced pressure and the residue is slurried in water (250 parts), collected and dried. 2-Cyano-4-nitro-4'-(N,N-diethylamino)azobenzene is obtained in 75% yield and requires no purification.

Workup

  1. temperatureheated
  2. temperatureThe temperatures is maintained at 110° C. for 31/
  3. custom2 hours when reaction
  4. customThe solvent is removed at 80° C. under reduced pressure
  5. customcollected
  6. customdried

Sources & evidence

ORD record
ord-99c02245faa74ee4a81ad4cfc92bd3be
Source dataset
uspto-grants-1980_09
Patent number
US04222935

Linked notes

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