Cyanogen Bromide → 1-(2-Methoxyethyl)-4,5-dihydro-1H-imidazol-2-amine hydrobromide

HRID 1726904Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][NH2:8].[N:9]#[C:10][Br:11]>>[BrH:11].[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]=[C:10]1[NH2:9]

Participants

Reactant 2

HCID 10476Cyanogen Bromide

HCID 18373882N-(2-methoxyethyl)ethylenediamine

Product 1

HCID 690265891-(2-Methoxyethyl)-4,5-dihydro-1H-imidazol-2-amine hydrobromideYield 88.8%

Procedure

Reaction of N-(2-methoxyethyl)ethylenediamine (16.0 g, 0.135 mol) (R. C. F. Jones and J. R. Nichols, Tetrahedron Lett., 1990, 31, 1767-1770) with cyanogen bromide (14.34 g, 0.135 mol) as described in the preparation of intermediate 6 gave 26.86 g (88% yield) of the title product as large white prisms (ethanol); mp 143-145° C.

Sources & evidence

ORD record: ord-58bcca3207fa48cb821afaf560a4aa07
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07494984B2

Reaction notes

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