N[C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1.[H+].[B-](F)(F)(F)[F:21].N([O-])=O.[Na+].NC(N)=O>O>[C:16]([C:13]1[CH:14]=[CH:15][C:9]2[CH:8]=[CH:7][C:6]3[CH:18]=[C:2]([F:21])[CH:3]=[CH:4][C:5]=3[S:11][C:10]=2[CH:12]=1)#[N:17]Suspend 6 gm. of the 3-cyano-8-aminodibenzo[b,f]thiepine from Example 18, Step 1, in 15 ml. of 50% fluoboric acid (HBF4) and 15 ml. of water. Cool the mixture to 3°-5° C. and slowly add 18 ml. of 10% sodium nitrite. Stir in the cold for 4 hours and add urea to destroy the excess sodium nitrite. Separate the solids by filtration and wash with cold 5% fluoboric acid followed by cold water and then ether. Air dry. Suspend the diazonium fluoroborate in 300 ml. of xylene and reflux for 2 hours with stirring. Filter and evaporate the filtrate to dryness. Triturate with ether to obtain the title product (m.p., 146°-148° C.).
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