Sodium ethoxide → HCID 20455140, compound

HRID 1902837Notes

Reaction equation

HRID 1902837 reaction equation
[Br:1][CH:2]([N:5]1[CH:9]=[CH:8][N:7]=[C:6]1[N+:10]([O-:12])=[O:11])[CH2:3]Br.CC[O-].[Na+]>CO>[Br:1][C:2]([N:5]1[CH:9]=[CH:8][N:7]=[C:6]1[N+:10]([O-:12])=[O:11])=[CH2:3]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 20455141HCID 20455141, compound

Product 1

HCID 20455140HCID 20455140, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20.1 g of 1-(1,2-dibromoethyl)-2-nitroimidazole were heated under reflux for 1 hour in 132 ml of a 0.51 N solution of sodium ethylate in methanol. The mixture was evaporated and the residue was taken up with 250 ml of ethyl acetate and 100 ml of water. The organic phase was washed with 100 ml of 10% sodium chloride solution and evaporated, and the residue was chromatographed on 300 g of silica gel using ethyl acetate/cyclohexane (4:1, v/v). After a forerun of 420 ml, there were isolated from 270 ml of further eluate 8.2 g of 1-(1-bromovinyl)-2-nitroimidazole; yield 4.6 g; m.p. 80°-82° C. (from isopropanol).

Workup

  1. customThe mixture was evaporated
  2. washThe organic phase was washed with 100 ml of 10% sodium chloride solution
  3. customevaporated
  4. customthe residue was chromatographed on 300 g of silica gel

Sources & evidence

ORD record
ord-b8b0f512c5ac4cb2a1454892bd8e768d
Source dataset
uspto-grants-1982_12
Patent number
US04366166

Reaction notes

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