Triethylamine → Perfluorophenyl 1-chloroisoquinoline-6-sulfonate

HRID 1473329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473329
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[OH:12].[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([S:24](Cl)(=[O:26])=[O:25])=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([S:24]([O:12][C:3]3[C:2]([F:1])=[C:7]([F:8])[C:6]([F:9])=[C:5]([F:10])[C:4]=3[F:11])(=[O:26])=[O:25])=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 861938101-Chloroisoquinoline-6-sulfonyl chloride

Produkt 1

HCID 86687382Perfluorophenyl 1-chloroisoquinoline-6-sulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,3,4,5,6-Pentafluorophenol (2.73 g, 14.82 mmol) was dissolved in DCM (49.4 ml). 1-chloroisoquinoline-6-sulfonyl chloride (2.59 g, 9.88 mmol) was added, followed by the dropwise addition of triethylamine (2.066 ml, 14.82 mmol). The reaction was stirred overnight at room temperature. The reaction was concentrated and purified by silica gel chromatography (40 g column, gradient elution 0 to 50% Et2O:Heptane) to afford perfluorophenyl 1-chloroisoquinoline-6-sulfonate as a white solid. m/z (ESI) 410.0 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel chromatography (40 g column, gradient elution 0 to 50% Et2O:Heptane)

Quellen und Nachweise

ORD-Eintrag
ord-769f01ae538b4f2fbf9cc92960830916
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012443B2

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