Sodium hydride → 2-(N-t-Butoxycarbonyl-N-methylamino)-4-(4-amino-3,5-dimethylphenoxy)nitrobenzene

HRID 1358582Notes

Reaction equation

HRID 1358582 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:24])[CH:15]=1>CN(C)C=O>[C:28]([O:27][C:25]([N:23]([C:16]1[CH:15]=[C:14]([O:9][C:5]2[CH:6]=[C:7]([CH3:8])[C:2]([NH2:1])=[C:3]([CH3:10])[CH:4]=2)[CH:19]=[CH:18][C:17]=1[N+:20]([O-:22])=[O:21])[CH3:24])=[O:26])([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 765434-Amino-3,5-dimethylphenolHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 181849972-(N-t-Butoxycarbonyl-N-methylamino)-4-(4-amino-3,5-dimethylphenoxy)nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-3,5-dimethylphenol (1.10 g) was added to a suspension of sodium hydride (0.35 g, 55% (w/w) dispersion in mineral oil) in anhydrous N,N-dimethylformamide and the mixture was stirred at room temperature for 15 minutes. To the mixture was added in small portions 4-chloro-2-(N-t-butoxycarbonyl-N-methylamino)-nitrobenzene and the mixture was stirred at 120° C. for 1 hour. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane: ethyl acetate=3:1 the eluant to afford the title compound (2.27 g, Rf=0.24: thin layer chromatography on a silica gel plate using hexane: ethyl acetate=3:1 as the eluant).

Workup

  1. stirringthe mixture was stirred at 120° C. for 1 hour
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and water The extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-7affea6ad8074fc4b52fff21ab2de911
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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