Triethylamine → 7-methoxy-3,4-dihydro-1H-isoquinoline-2-sulfonyl chloride

HRID 636946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636946
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].Cl.[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][CH2:16]2)=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]([S:1]([Cl:5])(=[O:3])=[O:2])[CH2:16]2)=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 27521977-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Produkt 1

HCID 226656767-methoxy-3,4-dihydro-1H-isoquinoline-2-sulfonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a stirred, precooled solution (-40° C.) of 0.41 mL of sulfuryl chloride in 10 mL of chloroform was added a mixture of 1.0 g of 7-methoxy-1,2,3,4-tetrahydro-isoquinoline-hydrochloride and 2.1 mL of triethylamine in 25 mL of chloroform at −40° C. Stirring was continued at −30° C. for one hour and additionally at 5° C. for one hour. The mixture was poured on ice, the organic layer extracted with cold water, dried (sodium sulfate) and concentrated. The residue was redissolved in diethyl ether and chromatographed on silica gel (isohexane/ethyl acetate=8/2 v/v) yielding 0.62 g of 7-methoxy-3,4-dihydro-1H-isoquinoline-2-sulfonyl chloride as an oil. EI-MS: 261 (M+).

Aufarbeitung

  1. additionThe mixture was poured on ice
  2. extractionthe organic layer extracted with cold water
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. dissolutionThe residue was redissolved in diethyl ether
  6. customchromatographed on silica gel (isohexane/ethyl acetate=8/2 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-69f30d8b5c3547e7bfd517abec3eec15
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194409B1

Notizen zur Reaktion

Wird geladen…