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Mercaptoacetonitrile → 11-Cyanomethylthio-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

HRID 232881
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 232881
[SH:1][CH2:2][C:3]#[N:4].O[CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)=[CH:20][C:7]1=2>FC(F)(F)C(O)=O.C(Cl)Cl.C(OCC)(=O)C>[C:3]([CH2:2][S:1][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)=[CH:20][C:7]1=2)#[N:4]
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Komponenten

6

Edukt 2

HCID 4346655MercaptoacetonitrileHCID 2335916711-Hydroxy-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

Produkt 1

HCID 2335915911-Cyanomethylthio-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepineAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 6422
Trifluoroacetic acid
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under ice cooling and stirring, 0.44 g of mercaptoacetonitrile was added to 2.22 g of 11-hydroxy-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine obtained in Reference example 45 dissolved in a mixed solution of 20 ml of trifluoroacetic acid and 10 ml of methylene chloride and the mixture was stirred at the same temperature for 1.5 hours. The residue obtained by condensing the reaction mixture under reduced pressure was dissolved in ethyl acetate and the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated saline solution and dried over anhydrous sodium sulfate. The viscous residue obtained by removing the solvent was crystallized from diethyl ether to obtain 1.23 g of the title compound.

Aufarbeitung

  1. customobtained in Reference example 45
  2. stirringthe mixture was stirred at the same temperature for 1.5 hours
  3. customThe residue obtained by condensing the reaction mixture under reduced pressure
  4. washthe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution
  5. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  6. customThe viscous residue obtained
  7. customby removing the solvent
  8. customwas crystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-90afd8ef592641ed97a12afedabac117
Quelldatensatz
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05591752

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