Triethylamine → 4-{[(2-chloro-3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-thiopyran-4-ol

HRID 44771

Reaktionsgleichung

Reaktionsgleichung von HRID 44771
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[NH2:23][CH2:24][C:25]1([OH:31])[CH2:30][CH2:29][S:28][CH2:27][CH2:26]1>ClCCl>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:23][CH2:24][C:25]2([OH:31])[CH2:30][CH2:29][S:28][CH2:27][CH2:26]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27851382,4-Dichloro-3-nitroquinolineHCID 459342884-(Aminomethyl)thian-4-ol

Produkt 1

HCID 866168654-{[(2-chloro-3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-thiopyran-4-olAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Under a nitrogen atmosphere triethylamine (3.91 mL, 28.0 mmol) was added to a chilled (0° C.) solution of 2,4-dichloro-3-nitroquinoline (7.22 g, 26.7 mmol) in dichloromethane (100 mL). A solution of 4-(aminomethyl)tetrahydro-2H-thiopyran-4-ol (4.12 g, 28.0 mmol) in dichloromethane (30 mL) was added dropwise. The reaction mixture was stirred at ambient temperature overnight and then concentrated under reduced pressure. The orange residue was combined with saturated aqueous sodium bicarbonate (50 mL) and ethyl acetate (40 mL), sonicated for 10 minutes, and then filtered. The isolated solid was washed extensively with water and then dried to provide 5.63 g of 4-{[(2-chloro-3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-thiopyran-4-ol as a yellow solid.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customsonicated for 10 minutes
  3. filtrationfiltered
  4. washThe isolated solid was washed extensively with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a77b4c6687a8443dabe3aa1084d8b2a3
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541438B2

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