4-Toluenesulfonyl chloride → HCID 67262961, Verbindung

HRID 1925474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1925474
ClC1C=C(C=CC=1)C(OO)=O.[Cl:12][CH2:13][C:14]1[N:15]([CH2:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1.[OH-].[NH4+:35].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl.O>[Cl:12][CH2:13][C:14]1[N:15]([CH2:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[C:18]([NH2:35])[C:17]=2[N:26]=1

Komponenten

7

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 672629742-(chloromethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline

Produkt 1

HCID 67262961HCID 67262961, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Chloroperoxybenzoic acid (mCPBA) (3.8 g of 77% pure material, 14.2 mmol) was added to a stirring solution of 2-(chloromethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline (3.0 g, 9.50 mmol) in dichloromethane (60 mL). After 15.5 hours, ammonium hydroxide (12 mL) and then p-toluenesulfonyl chloride (2.2 g, 11.4 mmol) were added to the stirring solution and the biphasic mixture was stirred at ambient temperature for 3 hours. The reaction was diluted with water (50 mL) and then transferred to a separatory funnel. The aqueous layer was extracted with dichloromethane (3×100 mL) and the combined organic fractions dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using a HORIZON HPFC system (silica cartridge, eluting with 3-20% methanol in dichloromethane) to provide 1.6 g of 2-(chloromethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a yellow solid.

Aufarbeitung

  1. customtransferred to a separatory funnel
  2. extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
  3. dry with materialthe combined organic fractions dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washa HORIZON HPFC system (silica cartridge, eluting with 3-20% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-678f37f3eea74cd8ae0bc1ee35ae8284
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178677B2

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