Sodium Iodide → 7-(2,5-Dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one

HRID 1700643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1700643
[Cl:1][C:2]1[S:3][C:4]([Cl:26])=[CH:5][C:6]=1[CH:7]1[CH2:12][C:11]([NH:13][NH:14]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:10][C:9](=[O:25])[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:34][C:35](=O)[CH3:36].[I-].[Na+]>COCCOC.CO>[Cl:1][C:2]1[S:3][C:4]([Cl:26])=[CH:5][C:6]=1[CH:7]1[CH2:12][C:11]2[N:13]=[N:14][CH:34]=[C:35]([CH3:36])[C:10]=2[C:9](=[O:25])[CH2:8]1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 183175305-(2,5-Dichlorothiophen-3-yl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one

Produkt 1

HCID 183174407-(2,5-Dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-oneAusbeute 52,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-(2,5-dichlorothiophen-3-yl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (1.33 g), anhydrous potassium carbonate (1.14 g), chloroacetone (0.4 g), sodium iodide (0.3 g), methanol (25 ml) and 1,2-dimethoxyethane (10 ml) was stirred at 80° C. for 3 hours. Under reduced pressure, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified with silica gel column chromatography to give 7-(2,5-dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one (0.51 g) as colorless crystals.

Aufarbeitung

  1. customUnder reduced pressure, the solvent was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified with silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a8b200322ef0446380401c22f4c8069a
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350749B1

Notizen zur Reaktion

Wird geladen…