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

HRID 1157080Notes

Reaction equation

HRID 1157080 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 C8H10N6O3: 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-f01e0fb09ffc4f4e9e7ee22879eae9b7
Source dataset
uspto-grants-2010_10
Patent number
US07807394B2

Reaction notes

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