Cyanogen Bromide → 2,4,6-Trimethylphenyl(imino)imidazolidine

HRID 1349404Notes

Reaction equation

HRID 1349404 reaction equation
[N:1]#[C:2]Br.[CH3:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[NH:13][CH2:14][CH2:15][NH2:16]>C(O)C>[CH3:12][C:7]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:5]([CH3:4])[C:6]=1[N:13]1[CH2:14][CH2:15][N:16]=[C:2]1[NH2:1]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 20780242N~1~-(2,4,6-Trimethylphenyl)ethane-1,2-diamine

Product 1

HCID 30171392,4,6-Trimethylphenyl(imino)imidazolidineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of cyanogen bromide (1.8 g, 18.5 mmol) in anhydrous ethanol (3 mL) was added at 0° C. to a solution of N1-(2,4,6-trimethyl-phenyl)-ethane-1,2-diamine (3.0 g, 16.9 mmol) in anhydrous ethanol (9 mL) under nitrogen. The reaction mixture was warmed up to room temperature for 10 min, then was heated at 155° C. for 40 min with a flow of nitrogen to remove ethanol. Upon cooling to r.t., the resulting solids were transferred to a separatory funnel via dichloromethane (70 mL), and washed sequentially with 1 N sodium hydroxide (2×35 mL), water and brine. The organic layer was dried over anhydrous sodium sulfate and solvents were removed in vacuo to afford the title compound as a pale white solid (3.08 g, 90% yield). The solids were used for the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ 6.70 (s, 2H), 3.46 (s, 4H), 2.06 (s, 3H), 1.99 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 160.1, 138.2, 137.8, 132.2, 129.5, 48.8, 43.5, 20.8, 17.5. LC/MS: tR=0.99 min., (MH+)=204.12.

Workup

  1. temperaturewas heated at 155° C. for 40 min with a flow of nitrogen
  2. customto remove ethanol
  3. temperatureUpon cooling to r.t.
  4. customthe resulting solids were transferred to a separatory funnel via dichloromethane (70 mL)
  5. washwashed sequentially with 1 N sodium hydroxide (2×35 mL), water and brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate and solvents
  7. customwere removed in vacuo

Sources & evidence

ORD record
ord-023ac0aa8d85455ea321baa90d00fe1c
Source dataset
uspto-grants-2007_05
Patent number
US07211669B2

Reaction notes

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