Benzene → HCID 21524633, compound

HRID 917972Notes

Reaction equation

HRID 917972 reaction equation
[CH3:1][N:2]1[C:6]([C:7]#[N:8])=[C:5]([N+:9]([O-:11])=[O:10])[N:4]=[C:3]1[CH2:12][OH:13].CC(O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O)=O.C1C=CC=CC=1>C(O)CO>[CH3:1][N:2]1[C:6]([C:7]#[N:8])=[C:5]([N+:9]([O-:11])=[O:10])[N:4]=[C:3]1[CH:12]=[O:13]

Participants

5

Reactant 3

HCID 241BenzeneHCID 14638340HCID 14638340, compoundHCID 16684437HCID 16684437, compound

Product 1

HCID 21524633HCID 21524633, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

0.91 G. (0.05 moles) of 1-methyl-2-hydroxymethyl-4-nitro-5-cyanoimidazole and 2.66 g. of leadtetraacetate are combined in 35 ml. of benzene and refluxed for 12 hours. 0.3 G. of ethylene glycol is added to the reaction mixture to consume excess leadtetraacetate and the reaction mixture is filtered. The benzene solution is washed with water and sodium bicarbonate solution, dried and evaporated to dryness. The residue is recrystallized from isopropanol affording 1-methyl-2-formyl-4-nitro-5-cyanoimidazole, m.p. 130° to 133C.

Workup

  1. customto consume excess leadtetraacetate
  2. filtrationthe reaction mixture is filtered
  3. washThe benzene solution is washed with water and sodium bicarbonate solution
  4. customdried
  5. customevaporated to dryness
  6. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-3eedd01118a24bc0b19b00beca9de834
Source dataset
uspto-grants-1976_07
Patent number
US03968228

Reaction notes

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