N-Methylaniline → N-methyl-N-(oxiran-2-ylmethyl)aniline

HRID 2294351Notes

Reaction equation

HRID 2294351 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:9]([CH:11]1[O:13][CH2:12]1)Br.[H-].[Na+]>CN(C)C=O>[CH3:1][N:2]([CH2:9][CH:11]1[CH2:12][O:13]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 18430EpibromohydrinHCID 24758Sodium hydride

Product 1

HCID 96044N-methyl-N-(oxiran-2-ylmethyl)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 46 was repeated, except that 5 g of N-methylaniline, 7.65 ml of epibromohydrin, 2.44 g of sodium hydride (as a 55% by weight dispersion in mineral oil) and 100 ml of anhydrous dimethylformamide were used, to give 1.67 g of the title compound as a pale yellow oil having an Rf value of 0.33 (on silica gel thin layer chromatography, using a 1:10 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 46

Sources & evidence

ORD record
ord-00beb2cf2a0c4554af03f04051bb6564
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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