3-Pyridinecarboxaldehyde → 3-[5-(4-Chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl]pyridine
Reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[S:7])=[CH:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=O)[CH:13]=1>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[S:7][CH:18]([C:14]3[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=3)[NH:9][N:8]=2)=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
39.2 g of p-chlorothiobenzoic acid hydrazide are dissolved in 350 ml of ethanol. Under nitrogen, 21.4 g of pyridine-3-aldehyde (dissolved in 20 ml of ethanol) are added dropwise to this solution. The reaction temperature is kept at 20° C. by cooling. When the addition is complete, the reaction mixture is stirred for 1 hour at reflux temperature and subsequently filtered through finely particulate diatomaceous earth. The filtrate is concentrated to three quarters of its initial volume and the precipitated product is isolated by filtration, washed with hexane and dried, affording the title compound of the formula ##STR8## with a melting point of 106°-108° C. (compound 1.1).