1,1-Bis(methylthio)-2-nitroethylene → 2-(Nitromethylidene)-1-[(pyridin-4-yl)methyl]hexahydropyrimidine
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH2:12])=[CH:3][CH:2]=1.[N+:13]([CH:16]=[C:17](SC)SC)([O-:15])=[O:14]>CO>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][NH:12][C:17]2=[CH:16][N+:13]([O-:15])=[O:14])=[CH:3][CH:2]=1Participants
4
Procedure
A mixture of N-(4-pyridylmethyl)trimethylenediamine (16.5 g), 1-nitro-2,2-bis(methylthio)ethylene (16.5 g) and methanol (100 ml) was refluxed for 2 hours with stirring. The generated gas was collected by an alkali trap. The reaction mixture was cooled to room temperature, and the resulting crystals were filtered to give 1-(4-pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine (16 g) of the following formula as pale yellow crystals. Concentrating the filtrate further gave 3 g of this compound.mp. 226°-228° C. ##STR14##