Indole → [2-(1H-Indol-3-ylsulfanyl)benzyl]methylamine

HRID 1994363

Reaktionsgleichung

Reaktionsgleichung von HRID 1994363
CN1[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3]1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.ClC(Cl)(Cl)C(O)=O.[OH-].[Na+].C(OCC)(=O)C.CO.[CH2:37]([N:39](CC)CC)C>C1COCC1.C(OCC)(=O)C>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[CH2:6][CH2:37][NH2:39])=[CH:12]1

Komponenten

8

Edukt 5

HCID 798IndoleHCID 6421Trichloroacetic AcidHCID 14798Sodium HydroxideHCID 124288082-Methyl-2,3-dihydro-benzo[d]isothiazoleHCID 21980445Ethyl acetate methanol triethylamine

Produkt 1

HCID 15979848[2-(1H-Indol-3-ylsulfanyl)benzyl]methylamineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Methyl-2,3-dihydro-benzoisothiazole (VI) (Hoffmann, R. W.; Goldman, S. Chem. Ber. 111, 1978, 2716-2725) (75 mg, 0.50 mmol) was dissolved in THF (1 mL) and added to indole (V) (140 mg, 0.60 mmol) under Ar. Tricloroacetic acid (90 mg, 0.55 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. 2 mL 1N NaOH (aq) was added. Extraction with ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent: ethyl acetate then ethyl acetate/methanol/triethylamine) gave 88 mg [2-(1H-Indol-3-ylsulfanyl)benzyl]methyl amine (67% yield).

Aufarbeitung

  1. extractionExtraction
  2. customwith ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent

Quellen und Nachweise

ORD-Eintrag
ord-fc32bc8f0bfa42c1a8aa4f517dea1c04
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652150B2

Verknüpfte Notizen

Wird geladen…