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

HRID 1389051Notes

Reaction equation

HRID 1389051 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-78a80a3141704a01979b1b1f417aae8e
Source dataset
uspto-grants-1981_01
Patent number
US04243667

Reaction notes

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