Sulfuric Acid → HCID 178458808, compound

HRID 51224Notes

Reaction equation

HRID 51224 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][NH:6][CH:7]=1)#N.[CH2:8]([Mg]Br)[CH3:9].S(=O)(=O)(O)[OH:13].[OH-].[Na+]>C1COCC1.O>[NH:6]1[CH:7]=[C:3]([C:1](=[O:13])[CH2:8][CH3:9])[N:4]=[CH:5]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178418443HCID 178418443, compoundHCID 178510437HCID 178510437, compound

Product 1

HCID 178458808HCID 178458808, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 4-cyanoimidazole (2 g, 21.4 mmol) in THF (25 ml) was added dropwise to a solution (68.5 mL, 68.5 mmol, 3.2 equivalents) of 1 M ethyl magnesium bromide in THF at 0 to 10° C. under a nitrogen atmosphere. The mixture was stirred at 15 to 25° C. for 4 h. Water (20 ml) and 10% aqueous sulfuric acid solution (45 ml) were successively added dropwise, and the mixture was stirred for 1 h. A 30% aqueous sodium hydroxide solution was added dropwise to adjust the pH to 8. After partitioning, the aqueous layer was extracted with ethyl acetate (15 ml×2). The organic layer was combined, and the mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and concentrated under reduced pressure. The concentration residue was broken up with n-hexane (6 ml), and the crystals were collected by filtration and washed with n-hexane. The crystals were dried in vacuo (40° C.) to give 1-(1H-imidazol-4-yl)-1-propanone (1.68 g, yield 63%).

Workup

  1. stirringthe mixture was stirred for 1 h
  2. customAfter partitioning
  3. extractionthe aqueous layer was extracted with ethyl acetate (15 ml×2)
  4. washthe mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  5. concentrationconcentrated under reduced pressure
  6. filtrationthe crystals were collected by filtration
  7. washwashed with n-hexane
  8. customThe crystals were dried in vacuo (40° C.)

Sources & evidence

ORD record
ord-1466c93b469b4d9ca855b18b6f79b078
Source dataset
uspto-grants-2004_03
Patent number
US06713632B1

Reaction notes

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