Carbon Disulfide → 4-(Tetrahydrofuran-2-ylmethylthiocarbamoylsulfanyl)-butyric acid methyl ester

HRID 352571

Reaktionsgleichung

Reaktionsgleichung von HRID 352571
[CH2:1]([NH2:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].[C:10](=[S:12])=[S:11].Cl[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]>CCO>[CH3:20][O:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][S:11][C:10](=[S:12])[NH:7][CH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][O:6]1

Komponenten

6

Edukt 4

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 76612Butanoic acid, 4-chloro-, methyl esterHCID 253298Tetrahydrofurfurylamine

Produkt 1

HCID 99037334-(Tetrahydrofuran-2-ylmethylthiocarbamoylsulfanyl)-butyric acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of tetrahydofurfurylamine (2 mL) in EtOH (20 mL) were added 5 N NaOH (3.9 mL) and carbon disulfide (1.17 mL), and the mixture was stirred for 1.5 h. Methyl 4-chlorobutyrate (2.4 mL) was then added, and the mixture was stirred overnight. Upon quenching with saturated NaCl solution the mixture was extracted with ether. Chromatography on silica gel gave the desired 4-(tetrahydrofuran-2-ylmethylthiocarbamoylsulfanyl)-butyric acid methyl ester product (1.1 g).

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. customUpon quenching with saturated NaCl solution the mixture
  3. extractionwas extracted with ether

Quellen und Nachweise

ORD-Eintrag
ord-4bd9eb844c2a4b3f994ea8ed6e3ff0e7
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747061B2

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