Water → 5-(2-((2-(5-Amino-1,3,4-thiadiazol-2-yl)ethyl)amino)ethyl)-1,3,4-thiadiazol-2-amine

HRID 1910465

Reaction equation

HRID 1910465 reaction equation
[NH:1]([CH2:6][CH2:7][C:8]#[N:9])[CH2:2][CH2:3][C:4]#[N:5].N[NH:11][C:12]([NH2:14])=[S:13].O.[OH-].[Na+]>C(O)(C(F)(F)F)=O>[NH2:11][C:12]1[S:13][C:4]([CH2:3][CH2:2][NH:1][CH2:6][CH2:7][C:8]2[S:13][C:12]([NH2:14])=[N:11][N:9]=2)=[N:5][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81493,3'-IminodipropionitrileHCID 14798Sodium HydroxideHCID 2723789Thiosemicarbazide

Product 1

HCID 39507595-(2-((2-(5-Amino-1,3,4-thiadiazol-2-yl)ethyl)amino)ethyl)-1,3,4-thiadiazol-2-amineYield 44.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 3,3′-iminodipropionitrile (1.50 g, 12.18 mmol) and thiosemicarbazide (2.22 g, 24.36 mmol) in TFA (10 mL) was heated at 85 for 4.5 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-(2-((2-(5-amino-1,3,4-thiadiazol-2-yl)ethyl)amino)ethyl)-1,3,4-thiadiazol-2-amine (1005, 1.47 g). 1H NMR (300 MHz, DMSO-d6) δ 6.95 (s, 4H), 2.90 (d, J=6.0 Hz, 4H), 2.83 (d, J=6.3 Hz, 4H).

Workup

  1. temperaturewas heated at 85 for 4.5 h
  2. filtrationThe white precipitate was collected by suction filtration
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-9b745f66cb134a159944825ce0ccfebd
Source dataset
uspto-grants-2013_12
Patent number
US08604016B2

Linked notes

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