Methyl iodide → HCID 22450431, Verbindung

Reaktionsgleichung

[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]([CH3:12])[C:8]([NH:10][CH3:11])=[S:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:17]I>C1COCC1>[CH3:17][S:9][C:8](=[N:10][CH3:11])[N:7]([CH2:6][C:5]1[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:12]

Komponenten

Versuchsvorschrift

In 50 ml of dry THF was dissolved 4.69 g (0.0205 mole) of N-(4-chlorobenzyl)-N-methyl-N′-methylthiourea, followed by addition of 0.82 g of 60% sodium hydride (oil). The mixture was refluxed for 1 hour. Then, under cooling with ice-water and stirring, 1.277 ml of methyl iodide was added dropwise and after completion of dropwise addition, the mixture was further stirred at room temperature for 45 minutes. The THF was distilled off and the residue was diluted with water (about 50 ml), saturated with sodium chloride, and extracted with AcOEt (100 ml×3). The extract was dried over MgSO4 and the solvent was distilled off to give 5.11 g of crude S-methyl-N-(4-chlorobenzyl)-N-methyl-N′-methylisothiourea as a colorless—pale yellow oil.