Reaktion #1920586

Reaktionsgleichung

3-(aminomethyl) indole

phosphorus pentachloride

hydrogen chloride

pyridine

ammonia

trichloroacetyl chloride

→

N-(3-indolylmethyl) trichloroacetamidine

Lösungsmittel

benzene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is heated
2. 2
   Temperaturat reflux for 30 minutes
3. 3
   Temperaturcooled
4. 4
   Einengenconcentrated to dryness in vacuo
5. 5
   Sonstigeto give a powder which
6. 6
   workup.ADDITIONis mixed well with 20.8 g
7. 7
   Temperaturwarmed to 90° C. for 30 minutes
8. 8
   Sonstigeto precipitate the product
9. 9
   SonstigeOvernight storage in the cold affords a solid which
10. 10
    Sonstigeis crystallized from benzene-hexane

Vorschrift

To a stirred solution of 14.6 g. (0.1 mole) of 3-(aminomethyl) indole in 30 ml. of benzene is added dropwise 18.2 g. (0.1 mole) of trichloroacetyl chloride over a period of approximately 5 minutes. The reaction mixture is heated at reflux for 30 minutes, cooled and concentrated to dryness in vacuo. The resultant solid is broken up and ground in a mortar to give a powder which is mixed well with 20.8 g. (0.1 mole) of phosphorus pentachloride. The mixture is heated in an oil bath at 110° C. until the evolution of hydrogen chloride ceases (approximately 3 hours). The reaction mixture containing the imidoyl chloride is cooled to room temperature and dry pyridine (7.9 g., 0.1 mole) is added followed by 6.5 ml. of concentrated aqueous ammonia. The reaction mixture is then stirred and warmed to 90° C. for 30 minutes, after which 100 ml. of water is added dropwise to precipitate the product. Overnight storage in the cold affords a solid which is crystallized from benzene-hexane to provide N-(3-indolylmethyl) trichloroacetamidine m.p. 135.5° to 138.5° C.

Quelle