2-[(Dimethylamino)methylidene]cyclohexane-1,3-dione → HCID 59490507, compound

HRID 2383409Notes

Reaction equation

HRID 2383409 reaction equation
[Na].CN([CH:5]=[C:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]1=O)C.Cl.[CH3:15][NH:16][C:17]([NH2:19])=[NH:18]>C(O)C>[CH3:15][NH:16][C:17]1[N:19]=[CH:5][C:6]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]=2[N:18]=1

Participants

5

Reactant 3

HCID 3593532-[(Dimethylamino)methylidene]cyclohexane-1,3-dioneHCID 5360545Sodium2×HCID 178485118HCID 178485118, compound

Product 1

HCID 59490507HCID 59490507, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To anhydrous ethanol (15 mL) was added sodium metal (0.45 g, 19.5 mmol). After complete dissolution of sodium metal in ethanol, 2-((dimethylamino)methylene)cyclohexane-1,3-dione (1 g, 5.5 mmol) and N-methylguanidine hydrochloride (1 g, 9.0 mmol) were added and the reaction was refluxed for 4 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Ice-cooled water (50 mL) was then added to the residue and the aqueous solution extracted with EtOAc (3×40 mL). The combined organic extract was dried using sodium sulfate and concentrated under reduced pressure to give the desired product (0.6 g, 57%) as a solid. The crude product was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz): δ 8.90 and 8.80 (2s, 1H), 5.98 and 5.82 (2s, 1H), 3.11 and 3.09 (2s, 3H), 2.96-2.88 (m, 2H), 2.58 (t, J=6.0 Hz, 2H), 2.10 (quintet, J=6.0 Hz, 2H). LCMS [M+H]: 178.

Workup

  1. additionwere added
  2. temperaturethe reaction was refluxed for 4 hours
  3. concentrationconcentrated under reduced pressure
  4. temperatureIce-cooled water (50 mL)
  5. additionwas then added to the residue
  6. extractionthe aqueous solution extracted with EtOAc (3×40 mL)
  7. extractionThe combined organic extract
  8. customwas dried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a39ed73542114a7d9acf836204493d56
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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