Potassium Carbonate → HCID 178463140, compound

HRID 1656868Notes

Reaction equation

HRID 1656868 reaction equation
CO[CH2:3][C:4]1[C:5]([CH3:13])=[C:6](I)[CH:7]=[CH:8][C:9]=1[S:10]C.[CH2:14]([N:16]1[C:20]([OH:21])=[CH:19][CH:18]=[N:17]1)[CH3:15].[C:22](=[O:25])([O-])[O-].[K+].[K+].[C]=O.O1[CH2:35][CH2:34]OCC1>C(N(CC)CC)C>[CH2:14]([N:16]1[C:20]([OH:21])=[C:19]([C:9](=[S:10])[C:8]2[CH:7]=[CH:6][C:5]([CH3:13])=[C:4]([CH2:3][O:25][CH3:22])[C:34]=2[CH3:35])[CH:18]=[N:17]1)[CH3:15]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 14801128HCID 14801128, compoundHCID 178418331HCID 178418331, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 178463140HCID 178463140, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.0 g of 3-methoxymethyl-2-methyl-4-methylthioiodobenzene, 1.46 g of 1-ethyl-5-hydroxypyrazole, 0.65 g of triethylamine, 4.04 g of anhydrous potassium carbonate, 0.28 g of dichloro(bistriphenylphosphine)palladium and 50 ml of 1,4-dioxane were charged into a 100 ml of Hastelloy autoclave equipped with a rotary stirrer, and the interior of autoclave was substituted with carbon monoxide, then, carbon monoxide was injected under a pressure of 10 kg/cm2. Then, the temperature was gradually raised under stirring, and the reaction was continued at 140° C. for 8 hours. The reaction mixture was left to cool, and then unreacted carbon monoxide was purged. The reaction solution was taken out, and the solvent was distilled off under reduced pressure. Then, water and chloroform were added, and the mixture was subjected to liquid separation. The aqueous layer was washed with chloroform, and insoluble substances were separated by filtration. Concentrated hydrochloric acid was added to bring the pH to a level of not higher than 1. Then, chloroform was added thereto, and the mixture was extracted twice. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 1.75 g of a crude of the desired product (yield: 84%). Oily substance.

Workup

  1. customequipped with a rotary stirrer
  2. temperatureThen, the temperature was gradually raised
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. customunreacted carbon monoxide was purged
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionThen, water and chloroform were added
  8. customthe mixture was subjected to liquid separation
  9. washThe aqueous layer was washed with chloroform, and insoluble substances
  10. customwere separated by filtration
  11. additionConcentrated hydrochloric acid was added
  12. additionThen, chloroform was added
  13. extractionthe mixture was extracted twice
  14. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  15. dry with materialdried over anhydrous sodium sulfate
  16. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2236c2473cd740c297f21e0ed242d346
Source dataset
uspto-grants-1993_10
Patent number
USRE034423

Reaction notes

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