N-Methylethylenediamine → N-(Diphenylmethyl)-1-methyl-4,5-dihydro-1H-imidazol-2-amine

HRID 225109

Reaction equation

HRID 225109 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4]N.I.[C:7]1([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:14][C:15](=[NH:18])SC)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>ClC1C=CC=CC=1Cl>[C:7]1([CH:13]([NH:14][C:15]2[N:2]([CH3:1])[CH2:3][CH2:4][N:18]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 8014N-MethylethylenediamineHCID 178504030HCID 178504030, compound

Product 1

HCID 12503394N-(Diphenylmethyl)-1-methyl-4,5-dihydro-1H-imidazol-2-amine

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To 7.41 grams (0.10 mole) of N-methylethylenediamine was added 38.43 grams (0.10 mole) of 1-(diphenylmethyl)-2-methyl-2-thiopseudourea hydroiodide in 250 milliliters of o-dichlorobenzene and the resulting mixture allowed to reflux overnight to produce the desired 2-diphenylmethylamino-1-methyl-2-imidazoline product. After completion of the heating, the solvent was removed by decantation and the residue purified by first dissolving in methanol containing activated carbon, replacing the methanol with isopropanol and diluting the isopropanol with acetone-ether to precipitate 16.55 grams (65 percent yield) of 2-diphenylmethylamino-1-methyl-2-imidazoline hydroiodide, m.p. 226°-228° C. After purification by treating with activated charcoal in methanol and recrystallizations from methanol-isopropanol, the product melted at (225°) 227°-229° C.

Workup

  1. temperatureto reflux overnight

Sources & evidence

ORD record
ord-152985d043d8448e8bd9063b0ce69d65
Source dataset
uspto-grants-1980_11
Patent number
US04235894

Linked notes

Loading…