Sodium hydride → t-Butyl N-[5-(4'-benzyloxybiphenyl-4-yloxy)-2-nitrophenyl]-N-methylcarbamate

HRID 2303877Notes

Reaction equation

HRID 2303877 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:23]1[CH:24]=[CH:25][C:26]([N+:38]([O-:40])=[O:39])=[C:27]([N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH:28]=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][C:23]3[CH:24]=[CH:25][C:26]([N+:38]([O-:40])=[O:39])=[C:27]([N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH:28]=3)=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 152688474-(4-Benzyloxyphenyl)phenolHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18461358t-Butyl N-[5-(4'-benzyloxybiphenyl-4-yloxy)-2-nitrophenyl]-N-methylcarbamateYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to that described in Reference Example 6, a reaction was carried out using 4′-benzyloxybiphenyl-4-ol (11.07 g), t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (11.5 g), sodium hydride (55 wt. %, 2.2 g) and anhydrous N,N-dimethylformamide/anhydrous tetrahydrofuran/anhydrous toluene=1/1/1 (360 ml) and the reaction mixture was purified to give the title compound (14.75 g).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-c5560c78de164882bca4a5232ba9f02c
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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