Acetonitrile → 4-Benzyloxy-3-aminocarbonylindole

HRID 325766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 325766
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.[C:21](=[N:23]S(Cl)(=O)=O)=[O:22].[OH-].[K+]>O>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([C:21]([NH2:23])=[O:22])=[CH:12][NH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6342Acetonitrile2×HCID 14797Potassium HydroxideHCID 70918Chlorosulfonyl isocyanateHCID 884654-(phenylmethoxy)-1H-indole

Produkt 1

HCID 127980094-Benzyloxy-3-aminocarbonylindole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4.4 g. 4-Benzyloxyindole (see Helv. Chim. Acta, 54. 2411/1971) are dissolved in 20 ml. anhydrous acetonitrile, cooled to 0° C. and mixed with 1.8 ml. N-carbonylsulphamoyl chloride in 20 ml. acetonitrile. After a reaction period of about 1 hour, a solution of 3.4 g. potassium hydroxide in 34 ml. water is added thereto and the reaction mixture then stirred for 1 hour at ambient temperature. After evaporating the solvent, the residue is taken up in 200 ml. 2 N hydrochloric acid and extracted with methylene chloride. From the methylene chloride extract there are obtained 4.8 g. (45% of theory) 4-benzyloxy-3-aminocarbonylindole, which is recrystallized from ethyl acetate; m.p. 176° C.

Aufarbeitung

  1. additionmixed with 1.8 ml
  2. customAfter a reaction period of about 1 hour
  3. customAfter evaporating the solvent
  4. extraction2 N hydrochloric acid and extracted with methylene chloride
  5. extractionFrom the methylene chloride extract there
  6. customare obtained 4.8 g
  7. custom(45% of theory) 4-benzyloxy-3-aminocarbonylindole, which is recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9ceef1eb7c5944b4af50cf9f5f9483cf
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04442295

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