Dimethylformamide → 1-Methoxymethyl-2-bromo-4-nitroimidazole

HRID 1158278Notes

Reaction equation

HRID 1158278 reaction equation
[Br:1][C:2]1[N:3]([CH2:11][O:12][CH3:13])[C:4](Br)=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.S([O-])([O-])=O.[Na+].[Na+].CN(C)C=O.C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C>[Br:1][C:2]1[N:3]([CH2:11][O:12][CH3:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 5422602,5-Dibromo-1-methoxymethyl-4-nitroimidazole

Product 1

HCID 166551311-Methoxymethyl-2-bromo-4-nitroimidazoleYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Suspension of 2,5-dibromo-1-methoxymethyl-4-nitroimidazole (17.15 g), sodium sulfite (13.73 g), dimethylformamide (100 ml) and water (50 ml) was stirred at a room temperature for 8 hours. The reaction mixture was neutralized with an aqueous solution being saturated with sodium hydrogencarbonate, then ethyl acetate and water were added. The organic layer was washed with an aqueous solution being saturated with sodium chloride, and dried over anhydrous sodium sulfate, then concentrated under a reduced pressure to obtain 2-bromo-1-methoxymethyl-4-nitroimidazole (11.17 g, yield: 86.8%) of white powdery product.

Workup

  1. washThe organic layer was washed with an aqueous solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-8ca17590e644481fbdb3902f307c4003
Source dataset
uspto-grants-2010_10
Patent number
US07807843B2

Reaction notes

Loading…