Hydrochloric Acid → 4-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine

HRID 2244962Notes

Reaction equation

HRID 2244962 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][CH:3]=1.Cl.[CH3:11][NH:12][CH2:13][CH2:14][NH2:15]>CO>[CH3:11][N:12]1[CH2:13][CH2:14][N:15]=[C:6]1[C:5]1[CH:8]=[CH:9][C:2]([NH2:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8014N-MethylethylenediamineHCID 133964-Aminobenzonitrile

Product 1

HCID 227288764-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamineYield 49.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-aminobenzonitrile (5.1 g, 43 mmol) in dry methanol (60 mL) at 0 C, hydrogen chloride gas was bubbled through until saturation was reached. The mixture was then stirred at room temperature overnight. It was concentrated in vacuo. The residue was dissolved in dry methanol (60 mL). To the solution, N-methyl ethylenediamine (19 mL, 216 mmol) was added. The mixture was then heated to reflux for 3 h. After being cooled in fridge overnight, the precipitated product was collected by filtration, then was dried on vacuum to give white solids (3.7 g). MS 176.0 (M+H).

Workup

  1. concentrationIt was concentrated in vacuo
  2. dissolutionThe residue was dissolved in dry methanol (60 mL)
  3. temperatureThe mixture was then heated
  4. temperatureto reflux for 3 h
  5. temperatureAfter being cooled in fridge overnight
  6. filtrationthe precipitated product was collected by filtration
  7. customwas dried on vacuum

Sources & evidence

ORD record
ord-6fd288883ee34f8499d1fd52141b360a
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

Loading…