Methyl iodide → N-(4-Methoxyphenyl)-2,4-dinitroaniline

HRID 1393608Notes

Reaction equation

HRID 1393608 reaction equation
[N+:1]([C:4]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:5]=1[NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([O-:3])=[O:2].[C:21](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[N+:1]([C:4]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:5]=1[NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:21])=[CH:9][CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 38580814-(2,4-Dinitroanilino)phenol

Product 1

HCID 260958N-(4-Methoxyphenyl)-2,4-dinitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.43 g of 4-(2,4-dinitroanilino)phenol, 500 mg of potassium carbonate and 0.32 ml of methyl iodide were stirred in 5 ml of N,N-dimethylformamide for 2 days at 20° C. The mixture was poured onto water, extracted three times with ethyl acetate, the extracts were dried on sodium sulfate, concentrated by evaporation in a vacuum, and the residue was chromatographed on silica gel.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted three times with ethyl acetate
  3. customthe extracts were dried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-aed33f363a99435c923858b1921c5c1d
Source dataset
uspto-grants-2008_03
Patent number
US07345075B2

Reaction notes

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