Potassium Carbonate → HCID 9866657, compound

HRID 1376171Notes

Reaction equation

HRID 1376171 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]([O-:14])([O-])=O.[K+].[K+].BrC[C:19]1[C:20]([CH2:25]Br)=[CH:21][CH:22]=[CH:23][CH:24]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>CC(C)=O.CN(C=O)C>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH2:11][C:23]2[CH:24]=[CH:19][C:20]([CH2:25][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:21][CH:22]=2)=[CH:9][CH:10]=1)(=[O:4])[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 66665o-Bis(bromomethyl)benzeneHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 9866657HCID 9866657, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

Hydroxyacetophenone (2 mmol) and 5 mmol of K2CO3 were stirred in 20 ml of acetone with 2 ml of DMF for 10 minutes. After addition of 3.5 mmol of α,α′-dibromoxylol the reaction was stirred at ambient temperature for 12 hours and after addition of 7 mmol of pyrrolidine for 1 hour under reflux. The solvent was evaporated under reduced pressure. The residue was suspended in water, extracted with methylene chloride. The combined organic extracts were crystallized with oxalic acid. Recrystallization resulted in the pure product.

Workup

  1. temperatureunder reflux
  2. customThe solvent was evaporated under reduced pressure
  3. extractionextracted with methylene chloride
  4. customThe combined organic extracts were crystallized with oxalic acid
  5. customRecrystallization
  6. customresulted in the pure product

Sources & evidence

ORD record
ord-1578bf6fb4d6426c8fbc4f1723ae691a
Source dataset
uspto-grants-2007_01
Patent number
US07169928B2

Reaction notes

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