Potassium Carbonate → 1-Oxo-2,3-dihydro-1H-indene-4-carboximidamide hydrochloride

HRID 1608580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1608580
F[B-](F)(F)F.C([O+](CC)CC)C.[C:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][CH2:19][C:20]2=[O:25])(=S)[NH2:14].C(=O)([O-])[O-].[K+].[K+].[Cl-:32].[NH4+:33]>C(Cl)Cl.O>[ClH:32].[C:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][CH2:19][C:20]2=[O:25])(=[NH:33])[NH2:14]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2723982Triethyloxonium tetrafluoroborateHCID 14950598HCID 14950598, Verbindung

Produkt 1

HCID 189379431-Oxo-2,3-dihydro-1H-indene-4-carboximidamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

10.8 g (54 mmol) of triethyloxonium tetrafluoroborate are added at room temperature under argon to a solution of 9.8 g (51.3 mmol) of 4-thiocarbamoyl-1-indanone in 500 ml of absolute methylene chloride. After 16 hours a mixture of 4.2 g of potassium carbonate and 4.2 ml of water is added to the reaction solution. The mixture is then stirred briefly and filtered, and the filtrate is washed with water. The organic phase is dried over magnesium sulfate, filtered and concentrated by evaporation. The resulting crude ethylthioimino ether is dissolved in 160 ml of absolute ethanol; 3.3 g (60 mmol) of ammonium chloride are added and the mixture is heated at reflux for 20 hours. After cooling, the reaction mixture is concentrated to dryness by evaporation. Starting compound (b) is purified by chromatography on 1000 ml of Amberlite®ER-180 resin (water as eluant) and recrystallised from ethanol/ether, m.p. 215°-218° (decomp.).

Aufarbeitung

  1. additionis added to the reaction solution
  2. filtrationfiltered
  3. washthe filtrate is washed with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. dissolutionThe resulting crude ethylthioimino ether is dissolved in 160 ml of absolute ethanol
  8. temperaturethe mixture is heated
  9. temperatureat reflux for 20 hours
  10. temperatureAfter cooling
  11. concentrationthe reaction mixture is concentrated to dryness by evaporation
  12. customStarting compound (b) is purified by chromatography on 1000 ml of Amberlite®ER-180 resin (water as eluant)
  13. customrecrystallised from ethanol/ether, m.p. 215°-218° (decomp.)

Quellen und Nachweise

ORD-Eintrag
ord-266835f912994d738dc84e9f05717272
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05395855

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