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

HRID 1531773Notes

Reaction equation

HRID 1531773 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-TriazoleYield 63%

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-compound (14.6 g, 63%), bp 110° C. at 6 mm 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

Sources & evidence

ORD record
ord-ee81f915aa1e495c9c84d354835914b2
Source dataset
uspto-grants-2001_03
Patent number
US06200975B1

Reaction notes

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