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

HRID 1011455Notes

Reaction equation

HRID 1011455 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C:10]#[CH:11])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[N:12]([CH:15](O)[CH3:16])=[N+:13]=[N-:14].[O:18]=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>[O-]S([O-])(=O)=O.[Cu+2].CO>[N+:1]([C:4]1[N:5]([CH2:9][C:10]2[N:14]=[N:13][N:12]([CH2:15][CH2:16][OH:18])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 22323701AzidoethanolHCID 23667548Sodium AscorbateHCID 546751432-Nitro-1-(prop-2-ynyl)-1H-imidazole

Product 1

HCID 575402032-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanolYield 76.3%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  1. additionthe reaction was poured onto EtOAc
  2. washwashed with NH4OH
  3. customthe residue was purified on a combiflash system

Sources & evidence

ORD record
ord-69cea252800d4c5fb8a2b73772a18337
Source dataset
uspto-grants-2011_07
Patent number
US07977361B2

Reaction notes

Loading…