Carbon Dioxide → HCID 86673329, compound

HRID 517357Notes

Reaction equation

HRID 517357 reaction equation
CN1CCN(C)[CH:3]1[C:8]1[S:9][CH:10]=[CH:11][C:12]=1[CH3:13].C([Li])CCC.CCCCCC.[C:25](=[O:27])=[O:26].C(=O)([O-])[O-:29].[K+].[K+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1.O.CN(C)C=O>[CH2:34]([O:26][C:25]([C:10]1[S:9][C:8]([CH:3]=[O:29])=[C:12]([CH3:13])[CH:11]=1)=[O:27])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 700904971,3-Dimethyl-2-(3-methylthiophen-2-yl)imidazolidineHCID 178418244HCID 178418244, compound

Product 1

HCID 86673329HCID 86673329, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,3-Dimethyl-2-(3-methylthiophen-2-yl)imidazolidine (3.1 g, 15.8 mmol) obtained in step 1 was dissolved in tetrahydrofuran (80 mL), 2.76N n-butyllithium/hexane solution (6.9 mL) was added dropwise at −78° C., and the mixture was stirred for 30 minutes. Dry ice was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, N,N-dimethylformamide (80 mL), potassium carbonate (6.54 g, 47.4 mmol), and benzyl bromide (8.0 g, 46.8 mmol) were added to the obtained residue, and the mixture was stirred at 60° C. for 3 hour. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (1.84 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. additionwere added to the obtained residue
  3. stirringthe mixture was stirred at 60° C. for 3 hour
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-772d7c7204b844fc9d2a07e9165c001d
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

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