F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([N:14]1[C:18](=[O:19])[NH:17][N:16]=[N:15]1)[CH2:12][CH3:13].C(=O)([O-])[O-].[Na+].[Na+].CS(C)=O>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:17]2[C:18](=[O:19])[N:14]([CH2:11][CH2:12][CH3:13])[N:15]=[N:16]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]A mixture of 38 parts of 1-fluoro-4-nitrobenzene, 32 parts of 1,4-dihydro-1-propyl-5H-tetrazol-5-one, 14 parts of sodium carbonate and 200 parts of dimethyl sulfoxide was stirred and heated for 4 hours at 120° C. The reaction mixture was cooled and poured into water. The precipitated product was filtered off and crystallized from 2-propanol, yielding 46 parts (74%) of 1,4-dihydro-1-(4-nitrophenyl)-4-propyl-5H-tetrazol-5-one; mp. 91.1° C. (int. 31).
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