Toluene → HCID 59135737, Verbindung

HRID 504962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504962
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19](=[S:21])[NH2:20])=[CH:15]2)(=[O:8])=[O:7].[C:22]([O:27][CH2:28][CH3:29])(=[O:26])[C:23]#[C:24][CH3:25].C(P(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>O1CCCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:21][CH:24]([CH2:23][C:22]([O:27][CH2:28][CH3:29])=[O:26])[CH2:25][N:20]=1)=[CH:15]2)(=[O:7])=[O:8]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 13831TributylphosphineHCID 78043Ethyl 2-butynoate2×HCID 57901763HCID 57901763, Verbindung

Produkt 1

HCID 59135737HCID 59135737, VerbindungAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (4.3 g), ethyl but-2-ynoate (3.2 mL) and tributylphosphine (3.2 mL) in tetrahydrofuran (40 mL)-toluene (40 mL) was stirred at room temperature for 2 days. ethyl but-2-ynoate (1.6 mL) was added to the reaction solution again, and the mixture was stirred at 60° C. for 2 hr. The reaction solution was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=2:8-4:6) to give the title compound (1.6 g, yield: 28%) as a pale-brown oil.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-46afffb057bc4624aecc1b9f1e063716
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07777047B2

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