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

HRID 538089

Reaction equation

HRID 538089 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-d731ef372b504249a8182a6dcfe22a2c
Source dataset
uspto-grants-2014_10
Patent number
US08865718B2

Linked notes

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