Sodium hydride → 1-(2-Methyl-5-pyrazinylmethyl)-2-(nitromethylene)imidazolidine

HRID 487922

Reaction equation

[N+:1]([CH:4]=[C:5]1[NH:9][CH2:8][CH2:7][NH:6]1)([O-:3])=[O:2].[H-].[Na+].[H][H].[CH3:14][C:15]1[CH:20]=[N:19][C:18]([CH2:21]Cl)=[CH:17][N:16]=1>CN(C)C=O.O>[CH3:14][C:15]1[CH:20]=[N:19][C:18]([CH2:21][N:6]2[CH2:7][CH2:8][NH:9][C:5]2=[CH:4][N+:1]([O-:3])=[O:2])=[CH:17][N:16]=1

Participants

Conditions

Temperature: 40 °C

Procedure

2-Nitromethyleneimidazolidine (12.9 g) was dissolved in dry dimethylformamide (100 ml), and at room temperature 60% oily sodium hydride (4.4 g) was added. The mixture was stirred at room temperature until the generation of hydrogen ceased. Then 2-methyl-5-pyrazinylmethyl chloride (14.3 g) was added at room temperature, and the mixture was stirred at 40° C. for 8 hours. After cooling to room temperature, the reaction mixture was added to 200 ml of water, and extracted with dichloromethane. On distilling off dichloromethane from the organic layer under reduced pressure, 1-(2-methyl-5-pyrazinylmethyl)-2-(nitromethylene)imidazolidine (5.4 g) was obtained as yellow crystals having a melting point of 163° to 166° C.

Workup

temperatureAfter cooling to room temperature
extractionextracted with dichloromethane
distillationOn distilling off dichloromethane from the organic layer under reduced pressure

Sources & evidence

ORD record: ord-3b8a034d74b74f97a1cfd4ab80ec6caa
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05298507

Linked notes

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