Water → 5,5'-Butane-1,4-Diylbis(1,3,4-Thiadiazol-2-Amine)

HRID 1910462Notes

Reaction equation

HRID 1910462 reaction equation
[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]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8128AdiponitrileHCID 14798Sodium HydroxideHCID 2723789Thiosemicarbazide

Product 1

HCID 574062125,5'-Butane-1,4-Diylbis(1,3,4-Thiadiazol-2-Amine)Yield 68.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

A 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).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe white precipitate was collected by suction filtration
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-8a8fbca8f879440887691fa9dbce35ef
Source dataset
uspto-grants-2013_12
Patent number
US08604016B2

Reaction notes

Loading…