Propargyl alcohol → HCID 10318611, Verbindung

HRID 1068019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1068019
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16](I)[CH:17]=3)[N:12]([CH3:22])[CH:11]=2)=[S:9])=[CH:4][CH:3]=1.[CH2:25]([OH:28])[C:26]#[CH:27]>C(NCC)C.[Cu](I)I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:27]#[C:26][CH2:25][OH:28])[CH:17]=3)[N:12]([CH3:22])[CH:11]=2)=[S:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 7859Propargyl alcoholHCID 21192539HCID 21192539, Verbindung

Produkt 1

HCID 10318611HCID 10318611, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

A suspension of N-(4-chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarbothioamide (0.20 g) from Preparation No. 44, propargyl alcohol (0.030 mL), copper iodide (0.028 g), and bis(triphenylphosphine)palladium(II)chloride (0.0095 g) in diethylamine (10 mL) is stirred at room temperature for 18 h. The solid in the reaction mixture is filtered, then dissolved in CH2Cl2/MeOH, and adsorbed onto silica. Purification by chromatography (eluent 1% MeOH:CH2Cl2 (1 L), 2% MeOH:CH2Cl2 (1 L)) affords the title compound as a yellow solid (0.12 g).

Aufarbeitung

  1. customfrom Preparation No
  2. filtrationThe solid in the reaction mixture is filtered
  3. dissolutiondissolved in CH2Cl2/MeOH
  4. customPurification by chromatography (eluent 1% MeOH:CH2Cl2 (1 L), 2% MeOH:CH2Cl2 (1 L))

Quellen und Nachweise

ORD-Eintrag
ord-7733e59cd787423fbfd7163097390032
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248739B1

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