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Sodium benzenethiolate → 1-[2-(phenylthio)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 433168
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 433168
Cl[CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[C:18]1([S-:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Na+]>CS(C)=O>[C:18]1([S:24][CH2:2][CH2:3][N:4]2[C:16]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]=[C:8]([NH2:17])[C:7]=3[N:6]=[CH:5]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 4110039Sodium benzenethiolateHCID 223204741-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 98582651-[2-(phenylthio)ethyl]-1H-imidazo[4,5-c]quinolin-4-amineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A round bottom flask was charged with a magnetic stir bar, 1-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine (2.0 g, 8.11 mmol), sodium benzenethiolate (1.79 g, 12.16 mmol), and anhydrous dimethyl sulfoxide (40 mL) under a nitrogen atmosphere. The reaction mixture was heated to 100° C. to give a homogeneous solution that was maintained at 100° C. for 30 minutes at which time the starting material was completely consumed. The hot solution was poured into rapidly stirred water (300 mL) which caused a solid to precipitate out of solution. The solid was collected by filtration to afford an off-white solid. The material was triturated with acetonitrile and collected by filtration to give 1-[2-(phenylthio)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (2.08 g, 6.49 mmol) as an off-white powder, m.p. 233-235° C.

Aufarbeitung

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customto give a homogeneous solution that
  3. temperaturewas maintained at 100° C. for 30 minutes at which time the starting material
  4. customwas completely consumed
  5. additionThe hot solution was poured into rapidly stirred water (300 mL) which
  6. customto precipitate out of solution
  7. filtrationThe solid was collected by filtration
  8. customto afford an off-white solid
  9. customThe material was triturated with acetonitrile
  10. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-654356f99eff4823bf522006eb1d1a8a
Quelldatensatz
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06667312B2

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