Thionyl Chloride → HCID 14624056, Verbindung

HRID 2051534

Reaktionsgleichung

Reaktionsgleichung von HRID 2051534
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:14].S(Cl)(Cl)=O>CN(C)C=O>[CH3:15][C:2]1([CH3:1])[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:13])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:14]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 146240553,3-dimethyl-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid

Produkt 1

HCID 14624056HCID 14624056, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideKatalysator

Versuchsvorschrift

8 g. 2,3-Dihydro-3,3-dimethyl-2-oxo-(1H)-indole-6-carboxylic acid and 1 drop of dimethylformamide were heated in 50 ml. thionyl chloride for 1 hour to the boil under reflux, the substance thereby going into solution. The thionyl chloride was removed under vacuum, the residue was suspended in dichloromethane and a solution of 1.6 ml. aniline and 2.7 ml. triethylamine in 30 ml. dichloromethane added dropwise thereto at an internal temperature of 15° C. The reaction mixture was stirred for 15 minutes at ambient temperature, the solvent was removed in a vacuum and the residue was digested with water, filtered off with suction and recrystallised from ethyl acetate. There were obtained 2.8 g. (56% of theory) of the title compound; m.p. 205-206° C.

Aufarbeitung

  1. customThe thionyl chloride was removed under vacuum
  2. additiondichloromethane added dropwise
  3. customat an internal temperature of 15° C
  4. customthe solvent was removed in a vacuum
  5. filtrationfiltered off with suction
  6. customrecrystallised from ethyl acetate
  7. customThere were obtained 2.8 g

Quellen und Nachweise

ORD-Eintrag
ord-69488d292d83427d827b47d552657cbf
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05019587

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