Water → 1-((2-(Trimethylsilyl)Ethoxy)Methyl)-1H-1,2,4-Triazole

HRID 382930Notes

Reaction equation

HRID 382930 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[CH3:8][Si:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][O:12][CH2:13]Cl.O>O1CCCC1.C(OCC)(=O)C>[CH3:8][Si:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][O:12][CH2:13][N:3]1[CH:7]=[N:6][CH:5]=[N:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 148754211-((2-(Trimethylsilyl)Ethoxy)Methyl)-1H-1,2,4-Triazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (4.63 g, 0.12 mol) in tetrahydrofuran (150 ml) was added 1,2,4-triazole (8.0 g, 0.12 mol) at room temperature under nitrogen. The mixture was cooled to 0° C. and 2-(trimethylsilyl)ethoxymethylchloride (20.5 ml, 0.12 mol) added dropwise. The mixture was stirred at room temperature overnight, water (100 ml) was added and the mixture diluted with ethyl acetate. The organic layer was dried ((MgSO4) and evaporated in vacuo and the residue distilled to give the title-compoud (14.6 g, 63%), bp 110° C. at 5mm Hg; 1H NMR (250 MHz, CDCl3) δ 0.01-0.03 (9H, s, 3 of CH3), 0.93 (2H, m, CH2), 3.63 (2H, m, CH2), 5.52 (2H, s, CH2), 7.99 (1H, s, Ar—H), 8.26 (1H, s Ar—H).

Workup

  1. dry with materialThe organic layer was dried ((MgSO4)
  2. customevaporated in vacuo
  3. distillationthe residue distilled
  4. customto give the title-compoud (14.6 g, 63%), bp 110° C. at 5mm Hg

Sources & evidence

ORD record
ord-311d2bcb00354545aea336cf7fdaa833
Source dataset
uspto-grants-2001_10
Patent number
US06310203B1

Reaction notes

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