Sodium Hydroxide → HCID 178490196, Verbindung

HRID 463775

Reaktionsgleichung

Reaktionsgleichung von HRID 463775
[OH-].[Na+].S(O)(O)(=O)=O.[CH:8]([NH:11][C:12]([NH2:14])=[NH:13])([CH3:10])[CH3:9].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31]([Cl:33])=[O:32])[CH:27]=[CH:28][CH:29]=1>CC(C)=O>[ClH:33].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31]([NH:13][C:12]([NH:11][CH:8]([CH3:10])[CH3:9])=[NH:14])=[O:32])[CH:27]=[CH:28][CH:29]=1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 27332463-Methoxyphenylacetyl chlorideHCID 178457611HCID 178457611, Verbindung

Produkt 1

HCID 178490196HCID 178490196, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

8.80 g of a 50% aqueous sodium hydroxide solution, isopropylguanidine sulfate (16.52 g), and 100 ml of acetone are stirred for 21/2 hrs at RT. The resulting mixture is then treated with anhydrous sodium sulfate (6.0 g) and stirring continued for 1 hr. A solution of 3-methoxyphenylacetyl chloride in 50 ml acetone is added to the mixture dropwise and the reaction mixture stirred at RT over the weekend. The mixture is filtered and the filtrate diluted with 100 ml of saturated aqueous sodium bicarbonate. The acetone solvent is evaporated in vacuo, the aqueous residue diluted with 100 ml of H2O and extracted with two 100 ml portions of methylene chloride. The combined organic extract is dried with sodium sulfate, filtered and evaporated in vacuo. The residual oil is stirred with 200 ml of diethyl ether. The resulting solid is collected, washed and diethyl ether, dried in air and recrystallized to afford 6.66 g of product, M.P. 156°-158° C.

Aufarbeitung

  1. stirringthe reaction mixture stirred at RT over the weekend
  2. filtrationThe mixture is filtered
  3. additionthe filtrate diluted with 100 ml of saturated aqueous sodium bicarbonate
  4. customThe acetone solvent is evaporated in vacuo
  5. additionthe aqueous residue diluted with 100 ml of H2O
  6. extractionextracted with two 100 ml portions of methylene chloride
  7. extractionThe combined organic extract
  8. dry with materialis dried with sodium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. stirringThe residual oil is stirred with 200 ml of diethyl ether
  12. customThe resulting solid is collected
  13. washwashed
  14. dry with materialdiethyl ether, dried in air
  15. customrecrystallized

Quellen und Nachweise

ORD-Eintrag
ord-a4daac2af10441018ce4508efc492ed4
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04544670

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