N,N'-Dimethylethylenediamine → 1,3-Dimethyl-2-imino-imidazolidine hydrobromide

HRID 66561Notes

Reaction equation

HRID 66561 reaction equation
[N:1]#[C:2][Br:3].[CH3:4][NH:5][CH2:6][CH2:7][NH:8][CH3:9]>C1(C)C=CC=CC=1>[BrH:3].[CH3:4][N:5]1[CH2:6][CH2:7][N:8]([CH3:9])[C:2]1=[NH:1]

Participants

4

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 10476Cyanogen Bromide

Product 1

HCID 134927221,3-Dimethyl-2-imino-imidazolidine hydrobromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 52.9 of cyanogen bromide in 300 ml of toluene is added dropwise in the course of 1 hour to a solution of 44.1 g (0.5 mol) of N,N'-dimethyl-ethylenediamine in 300 ml of toluene, with stirring. The reaction mixture is stirred for a further two hours at 80°. The mixture is allowed to cool to room temperature and is filtered and the residue is washed with ether. The crude 1,3-dimethyl-2-imino-imidazolidine hydrobromide obtained after drying in vacuo melts at 153°-160°.

Workup

  1. stirringThe reaction mixture is stirred for a further two hours at 80°
  2. filtrationis filtered
  3. washthe residue is washed with ether

Sources & evidence

ORD record
ord-e92997bc32f943b4b2c6e3a77ff35297
Source dataset
uspto-grants-1982_08
Patent number
US04342764

Reaction notes

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