4-Chloro-6-nitroquinoline-3-carbonitrile → 4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-6-nitro-quinoline-3-carbonitrile

HRID 1595819

Reaktionsgleichung

Reaktionsgleichung von HRID 1595819
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[S:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1)[NH2:21]>C(O)C>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][C:24]=1[S:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1

Komponenten

4

Edukt 2

HCID 110856904-Chloro-6-nitroquinoline-3-carbonitrileHCID 114590883-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamine

Produkt 1

HCID 699572994-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-6-nitro-quinoline-3-carbonitrileAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-3-quinolinecarbonitrile, 250 ml ethanol, and 6.18 g (25.8 mmol) 3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-aniline (WO-9615118) was heated to reflux under N2. Removed heat at 3½ hours and made basic with a solution of saturated sodium bicarbonate. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane and collected solids. Washed with water, dried in vacuo. Boiled solids in hexane to remove excess aniline, air dried. Boiled in 2 L ethyl acetate, and because of extreme insolubility, collected solids and dried in vacuo, giving 5.90 g of yellow solid: mass spectrum (electrospray m/e): M+H=437.2, 439.1.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 3½ hours
  5. customazeotroped with ethanol
  6. customcollected solids
  7. washWashed with water
  8. customdried in vacuo
  9. customto remove excess aniline, air
  10. customdried
  11. custombecause of extreme insolubility, collected solids
  12. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-85bd16a92baa41db879e55fb4b05271d
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288082B1

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