Water → HCID 57406041, compound

HRID 538088Notes

Reaction equation

HRID 538088 reaction equation
[C:1](#[N:7])[CH2:2][CH2:3][CH2:4][C:5]#[N:6].N[NH:9][C:10]([NH2:12])=[S:11].O.[OH-].[Na+]>C(O)(C(F)(F)F)=O>[CH2:2]([C:1]1[S:11][C:10]([NH2:12])=[N:9][N:7]=1)[CH2:3][CH2:4][C:5]1[S:11][C:10]([NH2:12])=[N:9][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10994GlutaronitrileHCID 14798Sodium HydroxideHCID 2723789Thiosemicarbazide

Product 1

HCID 57406041HCID 57406041, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of glutaronitrile (5.00 g, 53.13 mmol) and thiosemicarbazide (9.68 g, 106.26 mmol) in TFA (50 mL) was heated at 85° C. for 4 h. 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′-(propane-1,3-diyl)-bis(1,3,4-thiadiazol-2-amine) (1004, 13.72 g). 1H NMR (300 MHz, DMSO-d6) δ 7.06-7.03 (s, 4H), 2.87 (t, J=7.5 Hz, 4H), 2.02-1.95 (m, 2H).

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-98b470680ce742e1a0c36eeab900ed87
Source dataset
uspto-grants-2014_10
Patent number
US08865718B2

Reaction notes

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