Water → 5-[(2-Methylindolizin-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole

HRID 1440040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1440040
Cl.[N:2]1[C:6]2[CH2:7][CH2:8][CH:9]([C:11](N3CCCC3)=[O:12])[CH2:10][C:5]=2[NH:4][CH:3]=1.[CH3:18][C:19]1[CH:20]=[C:21]2[N:26]([CH:27]=1)[CH:25]=[CH:24][CH:23]=[CH:22]2.P(Cl)(Cl)(Cl)=O.O>ClCCCl>[CH3:18][C:19]1[CH:20]=[C:21]2[N:26]([C:27]=1[C:11]([CH:9]1[CH2:8][CH2:7][C:6]3[N:2]=[CH:3][NH:4][C:5]=3[CH2:10]1)=[O:12])[CH:25]=[CH:24][CH:23]=[CH:22]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 5826302-MethylindolizineHCID 18985210Pyrrolidin-1-yl(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-5-yl)methanone hydrochloride

Produkt 1

HCID 189852225-[(2-Methylindolizin-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazoleAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 0.50 g of N-[(4,5,6,7-tetrahydrobenzimidazol-5-yl)carbonyl]pyrrolidine hydrochloride and 0.39 g of 2-methylindolizine in 5 ml of 1,2-dichloroethane was added dropwise 0.90 g of phosphorus oxychloride. The reaction mixture was refluxed at 85° C. for one night. After cooling to room temperature, 5 ml of water was added thereto. The organic layer was removed, and 10 ml of chloroform was added to the aqueous layer. The solution was adjusted to a pH of 9 with a 20% aqueous solution of sodium hydroxide and then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography using chloroform/methanol as an eluent, followed by recrystallization from ethanol to obtain 0.21 g of 5-[(2-methylindolizin-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customThe organic layer was removed
  3. addition10 ml of chloroform was added to the aqueous layer
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation
  7. customThe residue was purified by silica gel column chromatography
  8. customfollowed by recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d45d0103751b472797c7571fc78324e7
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05496942

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