Sodium hydride → 1-(2-Chloro-5-pyridylmethyl)-2-methyl-3-nitroisothiourea

반응식

[CH3:1][S:2][C:3](=[N:5][N+:6]([O-:8])=[O:7])[NH2:4].[H-].[Na+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[CH:14][N:13]=1>CS(C)=O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:4][C:3](=[N:5][N+:6]([O-:8])=[O:7])[S:2][CH3:1])=[CH:14][N:13]=1

참가 물질

실험 절차

To a solution of 2-methyl-3-nitroisothiourea (15.0 g) in dimethylsulfoxide (100 ml) was gradually added sodium hydride (oil free 2.9 g) at 5° C., while being stirred for one hour. Thereafter, 2-chloro-5-chloromethyl pyridine (18.0 g) was added to the solution at a temperature in the range of from 5° to 10° C., followed by overnight stirring thereof at room temperature. After the dimethylsulfoxide in the solution was distilled off under reduced pressure, the resulting residue was purified on a chromatographic column (the eluent was a mixture of ethanol and chloroform), so as to obtain the desired 1-(2-chloro-5-pyridylmethyl)-2-methyl-3-nitroisothiourea (2.0 g) having a melting point in the range of from 141° to 143° C.