Nitrone → HCID 20347452, compound

HRID 1701274Notes

Reaction equation

HRID 1701274 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[N:16]=[N:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([Br:27])=[CH:20][C:19]=1Br)[N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])(=[O:3])[CH3:2].[CH2:29]=[N:30]O.N1C(C)=CC=CC=1C.[N+](C1C=CC=CC=1)([O-])=O>[Cu]I>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[N:16]=[N:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([Br:27])=[CH:20][C:19]=1[C:29]#[N:30])[N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6350NitroneHCID 7416NitrobenzeneHCID 79372,6-LutidineHCID 12525524N-{2-[(2,4-Dibromo-6-nitrophenyl)diazenyl]-5-(diethylamino)phenyl}acetamide

Product 1

HCID 20347452HCID 20347452, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 3-acetylamino-4-(2',4'-dibromo-6'-nitrophenylazo)-N,N-diethylaniline (5.3 parts), copper (I) iodide (1.9 parts), formaldoxime trimer (1.8 parts), 2,6-lutidine (2.15 parts), and nitrobenzene (100 parts), was heated to 90° C. for 10 hours when thin layer chromatography showed reaction to be effectively complete. The mixture was filtered, cooled, and the solvent was removed by steam distillation. Crystallisation of the solid product from ethanol gave 3-acetylamino-4-(2'-cyano-4'-bromo-6'-nitrophenylazo)-N,N-diethylaniline (Found; C, 49.5; H, 4.3; Br, 17.7; N, 18.3. C19H19BrN6O3 requires C, 49.65; H, 4.15; Br, 17.4; N, 18.3%)

Workup

  1. customreaction
  2. filtrationThe mixture was filtered
  3. temperaturecooled
  4. customthe solvent was removed by steam distillation
  5. customCrystallisation of the solid product from ethanol

Sources & evidence

ORD record
ord-448f66891caf484da2d52eab34452581
Source dataset
uspto-grants-1980_03
Patent number
US04192800

Reaction notes

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