Potassium Hydroxide → 5,5'-(Sulfonylbis(ethane-2,1-diyl))bis(1,3,4-thiadiazol-2-amine)

HRID 623718Notes

Reaction equation

HRID 623718 reaction equation
[S:1]([CH2:9][CH2:10][C:11](O)=O)([CH2:4][CH2:5][C:6](O)=O)(=[O:3])=[O:2].[NH2:14][NH:15][C:16]([NH2:18])=[S:17].[OH-].[K+]>>[S:1]([CH2:9][CH2:10][C:11]1[S:17][C:16]([NH2:18])=[N:15][N:14]=1)([CH2:4][CH2:5][C:6]1[S:17][C:16]([NH2:18])=[N:15][N:14]=1)(=[O:3])=[O:2]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 805123,3'-Sulfonylbis(propanoic acid)HCID 2723789Thiosemicarbazide

Product 1

HCID 867193735,5'-(Sulfonylbis(ethane-2,1-diyl))bis(1,3,4-thiadiazol-2-amine)Yield 20%

Procedure

3,3′-sulfonyldipropanoic acid (1 equivalent) and thiosemicarbazide (2 equivalents) were taken in PPA and refluxed for overnight. The reaction mixture was then cooled to room temperature. The pH of the reaction mixture was adjusted to 14 using aq. KOH solution, stirred for 30 min and filtered off the solid. The Solid obtained was triturated with diethyl ether and dried to afford the title compound I-15 in 20-30% yield.

Workup

  1. temperaturerefluxed for overnight
  2. filtrationfiltered off the solid
  3. customThe Solid obtained
  4. customwas triturated with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-b5b4502575474d468bd8a1b88cd8fc3c
Source dataset
uspto-grants-2016_04
Patent number
US09303002B2

Reaction notes

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