N,N'-Dimethylurea → 1-[2-(4-Cyanophenoxy)ethyl]-1-(2-hydroxyethyl)-3-methylurea

HRID 899131Notes

Reaction equation

HRID 899131 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[CH3:16][NH:17][C:18](NC)=[O:19]>>[C:12]([C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][OH:1])[C:18]([NH:17][CH3:16])=[O:19])=[CH:15][CH:14]=1)#[N:13]

Participants

3

Reactant 2

HCID 7293N,N'-DimethylureaHCID 690686254-{2-[(2-Hydroxyethyl)amino]ethoxy}benzonitrile

Product 1

HCID 690720791-[2-(4-Cyanophenoxy)ethyl]-1-(2-hydroxyethyl)-3-methylureaYield 54.3%

Conditions

Temperature
130 °C

Procedure

4-[2-(2-Hydroxyethylamino)ethoxy]benzonitrile (1 g, 0.009 mol; see Preparation C, step (ii) above) and N,N′-dimethylurea (0.43 g, 0.0049 mol) were heated with stirring at 130° C. for 4 h. The reaction was directly purified by column chromatography to yield 0.7 g of the sub-title product as an off white solid.

Workup

  1. customThe reaction was directly purified by column chromatography

Sources & evidence

ORD record
ord-3fcf4dca27f5419886967d6770579a05
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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