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Sodium hydride → N-Acetyl N-(3-(1-imidazolyl)phenyl)-2-nitro-4-iodoaniline

HRID 581933
Notes
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Reaction equation

HRID 581933 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[H][H].F[C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29]>CN(C=O)C.O>[C:1]([N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:6]=1)[C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29])(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 145905821-Fluoro-4-iodo-2-nitrobenzeneHCID 47215507N-Acetyl 3-(1-imidazolyl)anilineHCID 178418361HCID 178418361, compound

Product 1

HCID 53867634N-Acetyl N-(3-(1-imidazolyl)phenyl)-2-nitro-4-iodoanilineYield 25.3%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of 2e from Example 3 (30 g, 0.15 mol) in dry DMF (200 ml) is cooled to 0° C. under nitrogen. Sodium hydride (7.2 g of a 60% dispersion in mineral oil) is added portionwise. When the evolution of hydrogen has ceased a solution of 1c from Example 1 (52 g, 0.19 mol) in 50 ml DMF is added. The mixture is stirred at 120° C. for 5 hours and left at ambient temperature over night. The reaction mixture is poured into four volumes of water and the crude product is filtered off. Purification on silica gel using a mixture of ethyl acetate and petroleum ether (3:17) as the eluent affords pure 6c as an oil (17 g, 25%).

Workup

  1. additionis added
  2. waitleft at ambient temperature over night
  3. filtrationthe crude product is filtered off
  4. customPurification on silica gel using
  5. additiona mixture of ethyl acetate and petroleum ether (3:17) as the eluent

Sources & evidence

ORD record
ord-f538fa7077bf4921958068ba7091f7cc
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05922724

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes