Azidoethanol → 2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol

Participants

Role	Name	HCID	Charge
Reactant	Azidoethanol	HCID 22323701	—
Reactant	Sodium Ascorbate	HCID 23667548	—
Reactant	2-Nitro-1-(prop-2-ynyl)-1H-imidazole	HCID 54675143	—
Catalyst	Copper Sulfate	HCID 24462	—
Solvent	Methanol	HCID 887	—
Product	2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol	HCID 57540203	76.3%

Reaction Steps

To a round bottom flask was added nitropropyne 10 (150 mg, 0.99 mmol) and azido ethanol (86 mg, 0.99 mmol). To this flask was added CuSO4 (0.04M, 100 uL) and sodium ascorbate (0.1 M, 100 uL). After 16 hrs, the reaction was poured onto EtOAc and washed with NH4OH. The organics were combined and the residue was purified on a combiflash system using EtOAc:Hex as the eluent followed by DCM:MeOH to afford 180 mg (76.3% yield) of 11 as a clear colorless oil. Mass Spec (lo-res): Calc'd for C8H14N6O3: 238.08; found: 239.10 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07977361B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-69cea252800d4c5fb8a2b73772a18337
Source note	uspto-grants-2011_07