Reaktion #1154983

Reaktionsgleichung

guanidine hydrochloride

triethylamine

1-isopropyl-2-indolecarboxylic acid

carbonyldiimidazole

→

1-isopropyl-2-indoloyl-guanidine hydrochloride

Ausbeute 47.4%

Lösungsmittel

dimethylformamide

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat 45 to 50° C. for an hour
2. 2
   TemperaturAfter cooling to room temperature
3. 3
   workup.STIRRINGby stirring at room temperature for 12 hours
4. 4
   workup.DISTILLATIONThe mixture was then distilled off under reduced pressure and water
5. 5
   workup.ADDITIONwas added to the resulting residue
6. 6
   Extraktionthe mixture was extracted three times with ethyl acetate
7. 7
   TrocknenAfter drying over anhydrous magnesium sulfate
8. 8
   FiltrationThe precipitated crystals were filtered
9. 9
   Sonstigedried

Vorschrift

A tetrahydrofuran solution, 60 ml, containing 2.00 g (9.84 mmol) of 1-isopropyl-2-indolecarboxylic acid and 2.39 g (14.8 mmol) of carbonyldiimidazole was stirred at room temperature for 2 hours and then at 45 to 50° C. for an hour. After cooling to room temperature, 30 ml of a dimethylformamide solution of 5.64 g (59.0 mmol) of guanidine hydrochloride and 5.97 g (59.0 mmol) of triethylamine was added to the reaction mixture followed by stirring at room temperature for 12 hours. The mixture was then distilled off under reduced pressure and water was added to the resulting residue. After adjusting pH in the range of 5 to 6 with 2N hydrochloric acid, the mixture was extracted three times with ethyl acetate. After drying over anhydrous magnesium sulfate, the extract was acidified with hydrogen chloride/ether. The precipitated crystals were filtered and dried to give 1.31 g (47.4%) of the desired 1-isopropyl-2-indoloyl-guanidine hydrochloride.

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