[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11])[CH:5]=[N:4][N:3]=[N:2]1.N1C=CC=CC=1.S.O[S:21](O)(=O)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:11])=[S:21])[CH:5]=[N:4][N:3]=[N:2]1
5 g of 5-(tetrazol-1-yl)-valeric acid chloride are dissolved in 4.5 ml of absolute methylene chloride and, at 0°, this solution is added dropwise to 35.5 ml of a solution of pyridine and H2S in methylene chloride (30 ml of pyridine and 6 g of H2S in 100 ml of methylene chloride). The mixture is then stirred at 0° under a nitrogen atmosphere for 1 hour. The reaction mixture is taken up in chloroform, and the aqueous phase is acidified to pH 2 with 2N H2SO4 and extracted twice with chloroform. The combined organic phases are washed twice with 25 ml of 10% NaHCO3 solution. The pH is then adjusted to 3 with 2N H2SO4 and the title compound is obtained by repeated extraction with chloroform. It is dried over sodium sulphate and concentrated.
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