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

HRID 1092861
Notes
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Reaction equation

HRID 1092861 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
2×
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-cc45c9dceb3f499396d4926808a11a56
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129544B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes