Acetic Acid → HCID 21524667, compound

HRID 917968Notes

Reaction equation

HRID 917968 reaction equation
[CH3:1][N:2]1[C:6]([Br:7])=[C:5]([N+:8]([O-:10])=[O:9])[N:4]=[C:3]1COC(=O)C.[BrH:16].[C:17](O)(=O)[CH3:18]>>[CH3:1][N:2]1[C:6]([Br:7])=[C:5]([N+:8]([O-:10])=[O:9])[N:4]=[C:3]1[CH2:17][CH2:18][Br:16]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 21524651HCID 21524651, compound

Product 1

HCID 21524667HCID 21524667, compound

Procedure

0.596 G. (0.00214 moles) of 1-methyl-2-acetoxymethyl-4-nitro-5-bromoimidazole is dissolved in 20 ml. of acetic acid and treated with gaseous HBr for 5 minutes at room temperature. The reaction mixture is refluxed on a steam bath for 1 hour, cooled and evaporated to dryness. The residue is dissolved in chloroform, treated with 10% potassium bicarbonate solution. The chloroform layer is separated, dried and evaporated to dryness, affording 0.568 g. of 1-methyl-2-bromomethyl-4-nitro-5-bromoimidazole, recovered as an oil.

Workup

  1. temperatureThe reaction mixture is refluxed on a steam bath for 1 hour
  2. temperaturecooled
  3. customevaporated to dryness
  4. dissolutionThe residue is dissolved in chloroform
  5. additiontreated with 10% potassium bicarbonate solution
  6. customThe chloroform layer is separated
  7. customdried
  8. customevaporated to dryness
  9. customaffording 0.568 g
  10. customof 1-methyl-2-bromomethyl-4-nitro-5-bromoimidazole, recovered as an oil

Sources & evidence

ORD record
ord-c2336ee0e875408c8b38abee684871a1
Source dataset
uspto-grants-1976_07
Patent number
US03968228

Reaction notes

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