Phenethyl Isothiocyanate → 1-(1H-indol-5-ylmethyl)-3-phenethylthiourea

HRID 656259

Reaktionsgleichung

Reaktionsgleichung von HRID 656259
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:12]([N:20]=[C:21]=[S:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O.ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH:11][C:21]([NH:20][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[S:22])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

5

Edukt 2

HCID 16741Phenethyl IsothiocyanateHCID 54791(1H-indol-5-yl)methanamine

Produkt 1

HCID 590880511-(1H-indol-5-ylmethyl)-3-phenethylthioureaAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(1H-indol-5-yl)methylamine (8.5 mg) prepared in Step 1 was dissolved in dimethylformamide (100 μl) and the solution was diluted with dichloromethane (1 ml). To the diluted solution was added phenethylisothiocyanate (40 μl) and the mixture was stirred at room temperature for 2 hours. The resulting mixture was concentrated under reduced pressure and the obtained residue was chromatographed on a silica gel column eluting with ethyl acetate/hexane (2/3) to yield 1-(1H-indol-5-ylmethyl)-3-phenethylthiourea (15 mg, 83%).

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customthe obtained residue was chromatographed on a silica gel column
  3. washeluting with ethyl acetate/hexane (2/3)

Quellen und Nachweise

ORD-Eintrag
ord-f2de0c308d394d2782bb9941f6562262
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071650B2

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