O-(1,1-Dimethylethyl) S-(4,6-dimethyl-2-pyrimidinyl) carbonothioate → HCID 19960856, Verbindung

HRID 893854

Reaktionsgleichung

Reaktionsgleichung von HRID 893854
C(OC([CH:6]1[CH:14]2[C:9]3([CH:18]=[CH:17][CH:16]=[CH:15][C:10]3=[N:11][CH2:12][CH2:13]2)[S:8][CH2:7]1)=O)C.[C:19]([O:23][C:24](SC1N=C(C)C=C(C)N=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C(Cl)(Cl)Cl>[CH2:19]([O:23][C:24]([C:7]1([C:24]([O:23][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:25])[S:8][C:9]23[CH:18]=[CH:17][CH:16]=[CH:15][C:10]2=[N:11][CH2:12][CH2:13][CH:14]3[CH2:6]1)=[O:25])[CH3:20]

Komponenten

4

Edukt 2

HCID 148428O-(1,1-Dimethylethyl) S-(4,6-dimethyl-2-pyrimidinyl) carbonothioateHCID 19960928HCID 19960928, Verbindung

Produkt 1

HCID 19960856HCID 19960856, VerbindungAusbeute 123,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In 20 ml of desiccated chloroform were dissolved 6 g of 1,2,3,4-tetrahydro-benzo[b]thieno[2,3-c]pyridinecarboxylic acid ethyl ester synthesized in Example 1 and 6.63 g of 2-(tertiary-butoxycarbonylthio)-4,6-dimethylpyrimidine, and the solution was refluxed for 30 minutes. After distilling off chloroform under reduced pressure, the residue was dissolved in 300 ml of ethyl acetate and the solution was washed thrice with 50 ml of an aqueous 5% sodium hydrogencarbonate, twice with an aqueous 5% citric acid solution, and then twice with a saturated aqueous sodium chloride solution and thereafter dried with sodium sulfate. Ethyl acetate was distilled off under reduced pressure and the residue was recrystallized from a mixture of chloroform and petroleum ether to provide 6.18 g (yield of 76%) of 2 -tert-butoxycarbonyl-1,2,3,4-tetrahydro-benzo[b]thieno[2,3-c]pyridine-carboxylic acid ethyl ester.

Aufarbeitung

  1. temperaturethe solution was refluxed for 30 minutes
  2. distillationAfter distilling off chloroform under reduced pressure
  3. dissolutionthe residue was dissolved in 300 ml of ethyl acetate
  4. washthe solution was washed thrice with 50 ml of an aqueous 5% sodium hydrogencarbonate
  5. dry with materialtwice with an aqueous 5% citric acid solution, and then twice with a saturated aqueous sodium chloride solution and thereafter dried with sodium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customthe residue was recrystallized from a mixture of chloroform and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-bbe968fc67424876a0b172b66841c7de
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05126448

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