1,2-Bis(2-iodoethoxy)ethane → 1,2-bis(2-(3H-1,2,3-triazol-4-ylthio)ethoxy)ethane

HRID 2103944Notes

Reaction equation

HRID 2103944 reaction equation
I[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9]I.[SH:11][C:12]1[NH:16][N:15]=[N:14][CH:13]=1>C(O)C>[N:14]1[CH:13]=[C:12]([S:11][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][S:11][C:12]2[NH:16][N:15]=[N:14][CH:13]=2)[NH:16][N:15]=1

Participants

4

Reactant 2

HCID 5934361,2-Bis(2-iodoethoxy)ethaneHCID 178527741HCID 178527741, compound

Product 1

HCID 1784209301,2-bis(2-(3H-1,2,3-triazol-4-ylthio)ethoxy)ethaneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 ml of 1,2-bis(2-iodoethoxy)-ethane was dropped into the solution of 20 mmole 5-mercapto-1H-1,2,3-triazole (sodium salt) in 20 ml ethanol, and stirred for 24 hours at room temperature. After the solvent was evaporated in vacuum, the residual was separated with silica gel column. Elution with hexane/ethylacetate (1/3) first, and then with pure ethyl acetate gave 2.70 g product as viscous solid. Yield: 88%. 1H NMR (CDCl3): δ(ppm) 7.72 (2H, s), 3.74 (4H, t, JH-H=6.19), 3.65 (4H, s), 3.07 (4H, t, JH-H=6.19).

Workup

  1. customAfter the solvent was evaporated in vacuum
  2. customthe residual was separated with silica gel column
  3. washElution with hexane/ethylacetate (1/3) first

Sources & evidence

ORD record
ord-daa5aa3cc4414293803f006ab10e6f03
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

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