Thionyl Chloride → HCID 20330248, compound

Reaction equation

[C:1]([NH:8][NH:9][C:10](=[O:20])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=O.S(Cl)(Cl)=O>ClCCCl.C(Cl)Cl>[CH2:6]([O:5][C:3]([C:1]1[O:20][C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH3:19])=[CH:15][CH:16]=2)=[N:9][N:8]=1)=[O:4])[CH3:7]

Participants

Procedure

A solution of 22 g of 1-ethoxalyl-2-(4-ethoxybenzoyl)-hydrazine and 28 g of thionyl chloride in 157 ml of anhydrous 1,2-dichloroethane is heated under reflux, whilst stirring vigorously, until the evolution of gas has ceased (that is to say about 4 hours). The solvent and excess thionyl chloride are driven off in vacuo (50° C., 20 mm Hg). The residue is taken up in 150 ml of methylene chloride and the methylene chloride solution is successively washed with 2×30 ml of water, then with 30 ml of a 20% strength potassium bicarbonate solution and then with 2×30 ml of water. It is dried over anhydrous sodium sulphate. The solvent is driven off under reduced pressure (20 mm Hg, 50° C.). The solid residue is then recrystallized from isopropanol. 15.9 g of 2-ethoxycarbonyl-5-(4-ethoxyphenyl)-1,3,4-oxadiazole, which melts at 93° C., are obtained. The structure is confirmed by infrared spectrography.