Acetone → HCID 58894428, compound

HRID 716480Notes

Reaction equation

HRID 716480 reaction equation
C(O)C.[C:4]1([C:10](=O)[C:11](=O)[CH3:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:15]([NH2:18])[CH2:16][NH2:17].[OH-].[K+].[CH3:21][C:22]([CH3:24])=O>O>[CH:22]([C:16]1[N:17]=[C:11]([CH3:12])[C:10]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:18][CH:15]=1)([CH3:24])[CH3:21]

Participants

7

Reactant 5

HCID 180AcetoneHCID 702EthanolHCID 3301EthylenediamineHCID 113631-Phenyl-1,2-propanedioneHCID 14797Potassium Hydroxide

Product 1

HCID 58894428HCID 58894428, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 mL of dehydrated ethanol, 2.22 g of 1-phenyl-1,2-propanedione and 0.90 g of anhydrous ethylenediamine were put in an eggplant flask with a reflux pipe, and the inside air of the flask was substituted by argon. Then, it was irradiated with microwave (2.45 GHz, 1 to 100 W) for 10 minutes and reacted. Then, into this reacted solution, 2.20 mL of acetone and 1.01 g of potassium hydroxide were added, and irradiated with microwave (2.45 GHz, 1 to 100 W) for 20 minutes. Water was added into this mixture and an organic layer was extracted with ethyl acetate. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution after drying was filtrated and a solvent of the filtrate was distilled off. The obtained residue was purified by silicagel column chromatography using dichloromethane as a developing solvent, thereby obtaining an objective pyrazine derivative Hmppr-iPr (orange liquid, yield: 35%). For the irradiation of microwave, a microwave synthesis system (Discovery, manufactured by CEM Corporation) was used. A synthesis scheme of Step 1 is shown by the following (a-3).

Workup

  1. customThen, it was irradiated with microwave (2.45 GHz, 1 to 100 W) for 10 minutes
  2. customreacted
  3. customirradiated with microwave (2.45 GHz, 1 to 100 W) for 20 minutes
  4. extractionan organic layer was extracted with ethyl acetate
  5. washThe obtained organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. customThe solution after drying
  8. filtrationwas filtrated
  9. distillationa solvent of the filtrate was distilled off
  10. customThe obtained residue was purified by silicagel column chromatography

Sources & evidence

ORD record
ord-8138b3995e634cf0a29d48ae22a1c3dd
Source dataset
uspto-grants-2015_11
Patent number
US09187689B2

Reaction notes

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