Methanol → 5-(4-(2-(trimethoxysilyl)ethyl)benzylthio)-1H-1,2,3-triazole

HRID 2103955Notes

Reaction equation

HRID 2103955 reaction equation
[SH:1][C:2]1[NH:6][N:5]=[N:4][CH:3]=1.ClC[CH:9]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][Si:11]([O:16][CH3:17])([O:14][CH3:15])[O:12][CH3:13].[CH3:24]O>>[CH3:17][O:16][Si:11]([O:12][CH3:13])([O:14][CH3:15])[CH2:10][CH2:9][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][S:1][C:2]2[NH:6][N:5]=[N:4][CH:3]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 53426825((Chloromethyl)phenylethyl)-trimethoxysilaneHCID 178527741HCID 178527741, compound

Product 1

HCID 1785030005-(4-(2-(trimethoxysilyl)ethyl)benzylthio)-1H-1,2,3-triazoleYield 64.8%

Procedure

10 mmole of 5-mercapto-1H-1,2,3-triazole (sodium salt) was dissolved in 20 ml methanol and stirred for 5 minutes. 10 mmole of ((chloromethyl)phenylethyl)-trimethoxysilane was added to the solution, and stirred for 6 hours. The white precipitate was removed by filtration, the solvent in the filtrate was removed in vacuum. The filtrate was dissolved in small amount of methanol, and separated with a Si gel column (solvents: 5 ethylacetate/5 hexane in volume). 2.2 g product as liquid was obtained. Yield: 64.8%. 1H NMR (CDCl3) of Precursors 5: δ(ppm) 7.47 (1H, s), 7.12 (4H, m), 4.06 (2H, s), 3.55 (9H, s), 2.69 (2H, t, JH-H=8.50), 1.00 (2H, t, JH-H=8.50).

Workup

  1. stirringstirred for 6 hours
  2. customThe white precipitate was removed by filtration
  3. customthe solvent in the filtrate was removed in vacuum
  4. dissolutionThe filtrate was dissolved in small amount of methanol
  5. customseparated with a Si gel column (solvents: 5 ethylacetate/5 hexane in volume)

Sources & evidence

ORD record
ord-dad333a9167343bd914c0280500a7950
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

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