[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[CH:17]=1)#[N:2].[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+].CN(C=O)C>C(=O)([O-])[O-].[Na+].[Na+]>[NH:18]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]3[CH:12]=[CH:11][C:10]4[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=4[S:8][C:7]=3[CH:17]=2)=[N:2][N:20]=[N:19]1A mixture consisting of 4 g. 3-cyanodibenzo[b,f]thiepin (17 millimoles); 1.8 g. sodium azide (28 millimoles); 1.63 g. ammonium chloride (30.5 millimoles) and 50 cc. DMF is refluxed for 17 hours. The mixture is cooled and diluted with aqueous sodium carbonate solution. The solution is extracted with ether, then acidified with aqueous HCl solution. The tetrazole precipitates and is filtered. Crystallization from methanol affords 3.93 g. (83%) yellow product, m.p., 213° C.-214° C.
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