Cyanogen Bromide → HCID 13881444, compound

HRID 1164434Notes

Reaction equation

HRID 1164434 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][CH2:11][NH:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:20].[N:21]#[C:22][Br:23]>C1(C)C(C)=CC=CC=1>[BrH:23].[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:20])[C:22]1=[NH:21]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 3931947STK753189

Product 1

HCID 13881444HCID 13881444, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent3×

Procedure

500 ml of xylene are introduced into a 1 liter four-necked flask equipped with a stirrer, reflux condenser, thermometer and dropping funnel of 100 ml capacity. 72.5 g (0.27 moles) of 1,2-bis(2',6'-dimethylphenyl-amino)-ethane are dissolved in the xylene, and a solution of 33.9 g (0.32 moles) of cyanogen bromide in 200 ml of xylene is added dropwise, within about 1.5 hours, to the stirred solution at an internal temperature of 110° to 115° C. After the addition the mixture is stirred for a further hor at 110° to 115° C. and then it is allowed to cool. The separated precipitate is filtered off, washed with xylene and diethyl ether, and dried at room temperature. 100.5 g (99.4%) of 1,3-bis(2',6'-dimethylphenyl)-2-imino-imidazolidine hydrobromide are obtained as colourless crystals melting at 289°-290° C.

Workup

  1. customequipped with a stirrer
  2. temperaturereflux condenser
  3. additionAfter the addition the mixture
  4. temperatureto cool
  5. filtrationThe separated precipitate is filtered off
  6. washwashed with xylene and diethyl ether
  7. customdried at room temperature

Sources & evidence

ORD record
ord-6325869d95af4f0db3071062b0d0ca34
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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