Thionyl Chloride → HCID 178425534, Verbindung

HRID 1088437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088437
Cl.O[CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.S(Cl)(Cl)=O.[CH3:13][C:14]1([CH3:25])[CH2:23][CH:22]([CH3:24])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15]1>CN(C=O)C>[CH3:13][C:14]1([CH3:25])[CH2:23][CH:22]([CH3:24])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]1[CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 107292Quinoline, 1,2,3,4-tetrahydro-2,2,4-trimethyl-HCID 178418488HCID 178418488, Verbindung

Produkt 1

HCID 178425534HCID 178425534, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 10 ml of ethanol was dissolved 2.0 g (11.5 millimoles) of 1,2-dihydro-2,2,4-trimethylquinoline, and 0.4 g of 10% Pd-C was added to the solution and reaction was carried out at 60° C. in a hydrogen atmosphere for 7 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to obtain 1.8 g (the yield was 89%) of 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline in the form of a light-brown oil. To 0.5 g (3.7 millimoles) of 4-hydroxymethylimidazole hydrochloride was added 3 ml of thionyl chloride and reaction was carried out at 50° C. for 2 hours. The excess of thionyl chloride was removed by distillation under reduced pressure. The residue was dissolved in 10 ml of DMF and a solution of 1.1 g (6.3 millimoles) of 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline in 5 ml of DMF was added to the above solution at 100° C. Reaction was carried out for 1 hour. DMF was removed from the reaction mixture by distillation under reduced pressure. An aqueous solution of sodium hydrogen-carbonate was added to the residue and the mixture was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain a light-green oil. The oil was purified by the silica gel column chromatography (developing solvent; ethyl acetate) to obtain 0.35 g (the yield was 39%) of 4-[1-(2,2,4-trimethyl-1,2,3,4-tetrahydroquinolyl)methyl]imidazole in the form of a colorless crystal. Reaction was carried out in the same manner as described in Example 3 by using 4-[1-(2,2,4-trimethyl-1,2,3,4-tetrahydroquinolyl)methyl]imidazole to obtain 0.35 g (the yield was 30%) of intended compound No. 8 in the form of a light-brown oil.

Aufarbeitung

  1. customThe excess of thionyl chloride was removed by distillation under reduced pressure
  2. dissolutionThe residue was dissolved in 10 ml of DMF
  3. customReaction
  4. waitwas carried out for 1 hour
  5. customDMF was removed from the reaction mixture by distillation under reduced pressure
  6. additionAn aqueous solution of sodium hydrogen-carbonate was added to the residue
  7. extractionthe mixture was extracted with dichloromethane
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto obtain a light-green oil
  11. customThe oil was purified by the silica gel column chromatography (developing solvent; ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-26a3e1f696104ad6a6576185e66e0a3c
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04962200

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