Bromine → HCID 178433278, compound

HRID 1758752Notes

Reaction equation

HRID 1758752 reaction equation
[C:1]([C:4]1[NH:8][CH:7]=[N:6][C:5]=1[CH3:9])(=[O:3])[CH3:2].[Br:10]Br>Br>[CH3:9][C:5]1[N:6]=[CH:7][NH:8][C:4]=1[C:1](=[O:3])[CH2:2][Br:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 178467483HCID 178467483, compound

Product 1

HCID 178433278HCID 178433278, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent2×

Procedure

A solution of 1.57 g (12.6 mmol) of 5-acetyl-4-methylimidazole in 15 ml of concentrated hydrobromic acid was warmed to 50° and a solution of 2.01 g (12.6 mmol) of bromine in 15 ml of concentrated hydrobromic acid was added over 0.75 hour. The mixture was stirred at 50° for 1.25 hour, then concentrated. The residue was triturated with isopropyl alcohol and the white solid was collected by filtration. This amounted to 2.78 g (78%) of 1-(4-methyl-5-imidazolyl)-2-bromoethanone hydrobromide: nmr (D6DMSO) (δ): 9.40 (s, 1H); 4.87 (s, 2H); 2.65 (s, 3H). This material was converted to its free base by stirring for 15 minutes in 50 ml of saturated sodium bicarbonate solution to give, after collection by filtration and drying, 1-(4-methyl-5-imidazolyl)-2-bromoethanone as a white powder.

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with isopropyl alcohol
  3. filtrationthe white solid was collected by filtration
  4. stirringby stirring for 15 minutes in 50 ml of saturated sodium bicarbonate solution
  5. customto give
  6. customafter collection
  7. filtrationby filtration
  8. customdrying

Sources & evidence

ORD record
ord-62e035ca696e49f6b82f7d01790bed39
Source dataset
uspto-grants-1983_02
Patent number
US04374843

Reaction notes

Loading…