Potassium Carbonate → HCID 59228869, compound

HRID 1009190Notes

Reaction equation

HRID 1009190 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][N:3]2[C:7](=[O:10])[CH2:8][CH2:9][C@H:2]12.C(=O)([O-])[O-].[K+].[K+].I[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1>[Cu](I)I.CN(C)C=O>[CH3:24][C:21]1[CH:22]=[CH:23][C:18]([N:1]2[C:5](=[O:6])[CH2:4][N:3]3[C:7](=[O:10])[CH2:8][CH2:9][C@H:2]23)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 54488316(7aR)-dihydro-1H-Pyrrolo[1,2-a]iMidazole-2,5(3H,6H)-dione

Product 1

HCID 59228869HCID 59228869, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

In a 100 ml round bottomed flask fitted with a magnetical stirrer and a reflux condenser are placed 10 ml of dimethylformamide, 1.2 g of (R)-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-dione, 0.456 g of copper iodide, 1.2 g of potassium carbonate and 4.0 g of 1-iodo-4-methyl-benzene. The well stirred reaction mixture is heated at reflux for 4 hours. After cooling, the solvent is removed under vacuum (50° C., 7 mbar) and the residue is treated with 70 ml of ethyl acetate and the insoluble is filtered off. The organic solvent is then washed with 20 ml of saturated NaCl solution, dried over Na2SO4, filtered and evaporated under vacuum. The residue is triturated with 30 ml of diethyl ether and then crystallized with 20 ml of isopropanol, obtaining 0.92 g (y=47%) of the title compound as an off-white powder.

Workup

  1. customIn a 100 ml round bottomed flask fitted with a magnetical stirrer and a reflux condenser
  2. customreaction mixture
  3. temperatureis heated
  4. temperatureat reflux for 4 hours
  5. temperatureAfter cooling
  6. customthe solvent is removed under vacuum (50° C., 7 mbar)
  7. additionthe residue is treated with 70 ml of ethyl acetate
  8. filtrationthe insoluble is filtered off
  9. washThe organic solvent is then washed with 20 ml of saturated NaCl solution
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. customevaporated under vacuum
  13. customThe residue is triturated with 30 ml of diethyl ether
  14. customcrystallized with 20 ml of isopropanol

Sources & evidence

ORD record
ord-8e1e510e60ea4f6da32dc66997d1ac83
Source dataset
uspto-grants-2011_07
Patent number
US07973066B2

Reaction notes

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