Methyl iodide → tert-butyl N-(4-methoxy-2-nitrophenyl)-N-methylcarbamate

HRID 1419119Notes

Reaction equation

HRID 1419119 reaction equation
[H-].[Na+].[CH3:3]I.[C:5]([O:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22])=[O:11])([CH3:8])([CH3:7])[CH3:6]>CN(C)C=O>[C:5]([O:9][C:10]([N:12]([CH3:3])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22])=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10730597(4-Methoxy-2-nitro-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 53900404tert-butyl N-(4-methoxy-2-nitrophenyl)-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A procedure similar to that described in Preparation 7 was repeated, except that 0.46 g of sodium hydride (as a 55% w/w dispersion in mineral oil), 15 ml of dehydrated dimethylformamide, 0.66 ml of methyl iodide and a solution of 1.9 g of N-t-butoxycarbonyl-4-methoxy-2-nitroaniline (prepared as described in Preparation 22) in 15 ml of dehydrated dimethylformamide were used, to give 2.0 g of the title compound having an Rf value=0.34 (on thin layer chromatography on silica gel; developing solvent: a 1:5 by volume mixture of ethyl acetate and hexane).

Workup

  1. customA procedure similar to that described in Preparation 7

Sources & evidence

ORD record
ord-28fd0b672e29400aba0701893680bd62
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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