Methyl 4-(2-bromoacetyl)benzoate → HCID 178497551, compound

HRID 1061002Notes

Reaction equation

HRID 1061002 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)=O.C([NH:18][C:19]([NH2:21])=[NH:20])(=O)C>C(#N)C>[NH2:21][C:19]1[NH:18][CH:2]=[C:3]([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)[N:20]=1

Participants

4

Reactant 2

HCID 13612771Methyl 4-(2-bromoacetyl)benzoateHCID 178475102HCID 178475102, compound

Product 1

HCID 178497551HCID 178497551, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At room temperature, methyl 4-bromoacetylbenzoate (1.37 g) and acetylguanidine (1.62 g) were suspended in acetonitrile, followed by heating under reflux for 16 hours. The solvent was then distilled off under reduced pressure. Water was added to the residue. The insoluble matter so precipitated was collected by filtration, followed by washing with ethanol, whereby methyl 4-[2-aminoimidazol-4-yl]benzoate was obtained. The resulting product was dissolved in a mixed solvent of dioxane (10 ml) and 1N hydrochloric acid (10 ml), followed by heating under reflux for 8 hours. The residue obtained by distilling off the solvent was solidified by tetrahydrofuran and then collected by filtration, whereby the title compound (500 mg, 39%) was obtained.

Workup

  1. customAt room temperature
  2. temperatureby heating
  3. temperatureunder reflux for 16 hours
  4. distillationThe solvent was then distilled off under reduced pressure
  5. additionWater was added to the residue
  6. customThe insoluble matter so precipitated
  7. filtrationwas collected by filtration
  8. washby washing with ethanol

Sources & evidence

ORD record
ord-759cb40cecfa48f28697c95424a46f6c
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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