Sulfuric Acid → HCID 178450296, compound

HRID 51225Notes

Reaction equation

HRID 51225 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][NH:6][CH:7]=1)#N.[CH2:8]([Mg]Br)[CH2:9][CH3:10].S(=O)(=O)(O)[OH:14].[OH-].[Na+]>C1COCC1.O>[NH:6]1[CH:7]=[C:3]([C:1](=[O:14])[CH2:8][CH2:9][CH3:10])[N:4]=[CH:5]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178455851HCID 178455851, compoundHCID 178510437HCID 178510437, compound

Product 1

HCID 178450296HCID 178450296, compoundYield 83%

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 n-propyl 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 at 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 (12 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-butanone (2.45 g, yield 83%). 1H-NMR (CDCl3): δ 0.90 (3H, t, J=7.4 Hz), 1.60 (2H, q, J=7.3 Hz), 3.34 (2H, q, J=7.1 Hz), 7.77 (1H, s), 7.85 (1H, s)

Workup

  1. stirringthe mixture was stirred at 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-f682b53f88ff45ec8973086d838b4b5e
Source dataset
uspto-grants-2004_03
Patent number
US06713632B1

Reaction notes

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