2-Nitroimidazole → 2-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

HRID 2409622Notes

Reaction equation

[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl>C1COCC1>[N+:1]([C:4]1[N:5]([CH2:16][O:15][CH2:14][CH2:13][Si:12]([CH3:19])([CH3:18])[CH3:11])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 5 °C

Procedure

A suspension of 2-nitroimidazole (0.885 g, 7.8 mmol) and sodium hydride (60% dispersion in mineral oil, 0.440 g, 11.0 mmol, 1.4 equiv) in THF (20 mL) was stirred for 1.5 h at 5° C., under an argon atmosphere. 2-(Trimethylsilyl)ethoxymethyl chloride (1.5 mL, 8.6 mmol, 1.1 equiv) was then added. The reaction mixture was stirred for 2.5 h at 5° C., quenched by addition of a saturated aqueous solution of NH4Cl, and extracted with EtOAc. The combined organic phase was washed with H2O and brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:1) to afford 1.76 g of the title compound as a yellow oil: ES-MS: 244.1 [M+H]+; tR=4.63 min (System 1); TLC: Rf=0.19 (Hex/EtOAc, 3:1).

Workup

stirringThe reaction mixture was stirred for 2.5 h at 5° C.
customquenched by addition of a saturated aqueous solution of NH4Cl
extractionextracted with EtOAc
washThe combined organic phase was washed with H2O and brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:1)

Sources & evidence

ORD record: ord-3cf576e0c876416b95edb55b6b164c85
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815901B2

Reaction notes

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