Nitrone → HCID 20347454, compound

HRID 1701277Notes

Reaction equation

HRID 1701277 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]([CH3:24])=[CH:22][C:21]([Br:25])=[CH:20][C:19]=1Br)[N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])(=[O:3])[CH3:2].[CH2:27]=[N:28]O.[N+](C1C=CC=CC=1)([O-])=O>[Cu]I.C(N(CC)CC)C>[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]([CH3:24])=[CH:22][C:21]([Br:25])=[CH:20][C:19]=1[C:27]#[N:28])[N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6350NitroneHCID 7416NitrobenzeneHCID 12525525N-{2-[(2,4-Dibromo-6-methylphenyl)diazenyl]-5-(diethylamino)phenyl}acetamide

Product 1

HCID 20347454HCID 20347454, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 3-acetylamino-4-(2', 4'-dibromo-6'-methylphenylazo)-N,N-diethylaniline (4.8 parts), copper (I) iodide (2.0 parts), formaldoxime trimer (1.8 parts), triethylamine (1.5 parts), and nitrobenzene (100 parts) was heated to 90° C. for 11/2 hours when thin layer chromatography showed reaction to be complete. Isolation by the method of Example 3 gave 3-acetylamino-4-(2'-cyano-4'-bromo-6'-methylphenylazo)-N,N-diethylaniline, infra red spectrum identical with that of authentic material.

Workup

  1. customreaction

Sources & evidence

ORD record
ord-a616496d42a3440c8ed8749dd2594dfe
Source dataset
uspto-grants-1980_03
Patent number
US04192800

Reaction notes

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