N,N'-Dimethylethylenediamine → 1,3-Dimethyl-2-(3-methylthiophen-2-yl)imidazolidine

HRID 517356Notes

Reaction equation

HRID 517356 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH3:8])=O.[CH3:9][NH:10][CH2:11][CH2:12][NH:13][CH3:14]>C1(C)C=CC=CC=1>[CH3:9][N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH:1]1[C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 799113-Methyl-2-thiophenecarboxaldehyde

Product 1

HCID 700904971,3-Dimethyl-2-(3-methylthiophen-2-yl)imidazolidineYield 66.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

2-Formyl-3-methylthiophene (3.0 g, 23.8 mmol) and N,N′-dimethylethylenediamine (2.3 g, 26.2 mmol) were dissolved in toluene (80 mL), and the mixture was stirred at 120° C. overnight. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give the title compound (3.1 g, 15.8 mmol).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c5c5293b7e5648e78e930210ae75cb8c
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

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