Chloromethyl ethyl ether → 1-Ethoxymethyl-3-methylthio-1,2,4-triazole

HRID 850106Notes

Reaction equation

HRID 850106 reaction equation
[CH3:1][S:2][C:3]1[NH:7][N:6]=[CH:5][N:4]=1.[CH2:8]([O:10][CH2:11]Cl)[CH3:9]>C1(C)C=CC=CC=1>[CH2:8]([O:10][CH2:11][N:6]1[CH:5]=[N:4][C:3]([S:2][CH3:1])=[N:7]1)[CH3:9]

Participants

4

Reactant 2

HCID 18523Chloromethyl ethyl etherHCID 5753783-Methylthio-4H-1,2,4-triazole

Product 1

HCID 193659541-Ethoxymethyl-3-methylthio-1,2,4-triazoleYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 5-methylthio-1,2,4-triazole (6.19, 53 mmol) and chloromethyl ethyl ether (2.5 ml, 26 mmol) in toluene (40 ml) was stirred at room temperature for 24 hours. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was chromatographed on silica by elution with ethyl acetate/diethylamine (95:5) to yield the title compound (1.1 g, 27%), as a colourless oil, which was characterised by

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was chromatographed on silica by elution with ethyl acetate/diethylamine (95:5)

Sources & evidence

ORD record
ord-89716f5e9a584abf9019026f1c6abb45
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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