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Tin tetrachloride → Ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate

HRID 2423528
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2423528
[Sn](Cl)(Cl)(Cl)Cl.[Br:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:10]=[CH:11][CH:12]=1.Cl[CH:26](SC)[C:27]([O:29][CH2:30][CH3:31])=[O:28]>ClCCl.ClCCCl>[Br:6][C:7]1[CH:8]=[C:9]2[C:10](=[CH:11][CH:12]=1)[CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:15]([S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17])[CH2:14][CH2:13]2.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:8]=1[CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:15]([S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17])[CH2:14][CH2:13]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 24287Tin tetrachlorideHCID 10877535Ethyl 2-chloro-2-(methylsulfanyl)acetateHCID 59321588N-[2-(3-bromophenyl)ethyl]benzenesulfonamide

Produkt 2

HCID 59321554Ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylateAusbeute 79 %HCID 59321590Ethyl 8-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate
Ausbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Tin(IV)chloride (6.67 mL of a 1 M solution in dichloromethane, 6.67 mmol) was added to N-[2-(3-bromophenyl)ethyl]benzenesulfonamide (1.08 g, 3.17 mmol) and ethyl chloro(methylthio)acetate (1.07 g, 6.35 mmol) in 1,2-dichloroethane (11 mL) under argon and the reaction was heated at reflux for 3 hours. After cooling, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:4 ethyl acetate:hexanes to give 1.07 g (79%) of ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate and 255.6 mg (19%) of ethyl 8-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate as oils.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium bicarbonate and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 1:4 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cf374c60b32f45cfa6cf4a4d05e4f2ab
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07960552B2

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