[C:1](#[N:8])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].N[NH:10][C:11]([NH2:13])=[S:12].O.[OH-].[Na+]>FC(F)(F)C(O)=O>[CH2:2]([C:1]1[S:12][C:11]([NH2:13])=[N:10][N:8]=1)[CH2:3][CH2:4][CH2:5][C:6]1[S:12][C:11]([NH2:13])=[N:10][N:7]=1A mixture of adiponitrile (8.00 g, 73.98 mmol) and thiosemicarbazide (13.48 g, 147.96 mmol) in trifluoroacetic acid (TFA) (75 mL) was heated at 80° C. for 17 hours. The reaction was cooled to room temperature and poured into a mixture of ice and water. Sodium hydroxide pellets were added to the mixture until it was basic (pH 14). The white precipitate was collected by suction filtration, rinsed with water and dried to provide 5,5′-(butane-1,4-diyl)-bis(1,3,4-thiadiazol-2-amine) (1001, 13.07 g). 1H NMR (300 MHz, DMSO-d6) δ 7.00 (s, 4H), 2.84 (bs, 4H), 1.68 (bs, 4H).
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