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

HRID 2303853Notes

Reaction equation

HRID 2303853 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].Cl[C:12]1[CH:13]=[CH:14][C:15]([N+:27]([O-:29])=[O:28])=[C:16]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:17]=1.[H-].[Na+]>CN(C)C=O>[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][C:12]2[CH:13]=[CH:14][C:15]([N+:27]([O-:29])=[O:28])=[C:16]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:17]=2)=[CH:4][C:3]=1[CH3:10]

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)nitrobenzeneYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By using 1.10 g of 4-amino-3,5-dimethylphenol, 2.29 g of t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate, 0.35 g of sodium hydride (55% by weight) and 30 ml of anhydrous N,N-dimethylformamide, reaction and purification were carried out in a similar manner to that described in Reference Example 6, whereby 2.27 g of the title compound were obtained.

Sources & evidence

ORD record
ord-1f5def646059497786910081e9c84592
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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