3-Phenylphenol → t-Butyl N-methyl-N-[2-nitro-5-(3-phenylphenoxy)phenyl]carbamate

HRID 2303871Notes

Reaction equation

HRID 2303871 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:15]1[CH:16]=[CH:17][C:18]([N+:30]([O-:32])=[O:31])=[C:19]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:20]=1.[H-].[Na+]>CN(C)C=O>[CH3:29][N:21]([C:19]1[CH:20]=[C:15]([O:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]=2)[CH:16]=[CH:17][C:18]=1[N+:30]([O-:32])=[O:31])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 113813-PhenylphenolHCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18461261t-Butyl N-methyl-N-[2-nitro-5-(3-phenylphenoxy)phenyl]carbamateYield 91.3%

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-phenylphenol (4.0 g), t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (6.5 g), sodium hydride (55 wt. %, 1.13 g) and anhydrous N,N-dimethylformamide (35 ml) and the reaction mixture was purified to give the title compound (8.7 g).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-715f0fa7271048ae95f1f96f547dfa57
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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