Methyl p-toluenesulfonate → 1-Methyl-2-methylthioquinolinium p-toluenesulfonate

HRID 2121951

Reaktionsgleichung

Reaktionsgleichung von HRID 2121951
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]1=[S:12].[C:13]1([CH3:24])[CH:18]=[CH:17][C:16]([S:19]([O:22]C)(=[O:21])=[O:20])=[CH:15][CH:14]=1>>[C:13]1([CH3:24])[CH:14]=[CH:15][C:16]([S:19]([O-:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1.[CH3:1][N+:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[S:12][CH3:13]

Komponenten

3

Edukt 2

HCID 6645Methyl p-toluenesulfonateHCID 7414191-Methyl-2(1H)-quinolinethione

Produkt 1

HCID 155970931-Methyl-2-methylthioquinolinium p-toluenesulfonateAusbeute 193,6 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 1-methylquinolin-2-thione (175 mg, 1.0 mmol) and methyl p-toluenesulfonate (186 mg, 1.0 mmol) were heated at 130° C. After 30 min the resulting solid was cooled, crushed, triturated with Et2O (4×1 mL) and dried under high vacuum to give the title compound (0.35 g, 97%) as a white solid. 1H-NMR (DMSO-d6): δ 8.96 (1H, d), 8.46 (1H, d), 8.35 (1H, dd), 8.16 (1H, m), 8.08 (1H, d), 7.91 (1H, m), 7.47 (2H, d), 7.10 (2H, d), 4.40 (3H, s), 3.02 (3H, s), 2.28 (3H, s).

Aufarbeitung

  1. temperatureAfter 30 min the resulting solid was cooled
  2. customcrushed
  3. customtriturated with Et2O (4×1 mL)
  4. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8dbea428755a4e65b0fd368ac6be3d60
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06696473B2

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