3-(Dimethylamino)phenol → t-Butyl N-[5-(3-dimethylaminophenoxy)-2-nitrophenyl]-N-methylcarbamate

HRID 2303865Notes

Reaction equation

HRID 2303865 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.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>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][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]([CH3:22])([CH3:23])[CH3:24])[CH:17]=1

Participants

5

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18461334t-Butyl N-[5-(3-dimethylaminophenoxy)-2-nitrophenyl]-N-methylcarbamateYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to that described in Reference Example 6, a reaction was carried out using 3-dimethylaminophenol (0.82 g), t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (1.72 g), sodium hydride (55 wt. %, 0.26 g) and anhydrous N,N-dimethylformamide (50 ml) and the reaction mixture was purified to give the title compound (2.17 g).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-36aa7ddd0eba43589552a39220082e61
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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