Cyanogen Bromide → 4-(3-Bromophenyl)-1,4-dimethylimidazolidin-2-imine

HRID 73264Notes

Reaction equation

HRID 73264 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:13])([CH3:12])[CH2:9][NH:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.Br[C:15]#[N:16]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:12])[CH2:9][N:10]([CH3:11])[C:15](=[NH:16])[NH:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 673044282-(3-bromophenyl)-N1-methylpropan-1,2-diamine

Product 1

HCID 1784801884-(3-Bromophenyl)-1,4-dimethylimidazolidin-2-imineYield 104.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(3-bromophenyl)-N1-methylpropan-1,2-diamine (0.12 g, 0.50 mmol) in EtOH (10 mL) was added BrCN (0.073 g, 0.70 mmol, 1.4 eq). The mixture was stirred at RT for 16 h and then concentrated in vacuo. The residue was redissolved in CHCl3 (20 mL) and the solution was washed with 15% NaOH (10 mL). The aqueous layer was extracted with CHCl3 (3×10 mL) and the combined organic layer was dried (MgSO4), and concentrated to give 0.14 g (100%) of 4-(3-bromophenyl)-1,4-dimethylimidazolidin-2-imine (CD4; R1=Me, R4=Me) as a colorless oil. 1H NMR (CDCl3) δ 7.42 (t, J=1.7 Hz, 1H), 7.35 (dd, J=8.1, 1.7 Hz, 2H), 7.15 (t, J=8.1 Hz, 1H), 3.62 (d, J=9.3 Hz, 1H), 3.53 (d, J=9.0 Hz, 1H), 3.08 (s, 3H), 1.56 (bs, 3H). MS (ESI) m/e 268.1, 270.1 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was redissolved in CHCl3 (20 mL)
  3. washthe solution was washed with 15% NaOH (10 mL)
  4. extractionThe aqueous layer was extracted with CHCl3 (3×10 mL)
  5. dry with materialthe combined organic layer was dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f5f6b71aefc4c51a7e38ce7d137fc4a
Source dataset
uspto-grants-2014_09
Patent number
US08829036B2

Reaction notes

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