StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Carbon Disulfide → n-Hexyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65067
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 65067
[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][NH:4]1.C(N(CC)CC)C.[C:23](=[S:25])=[S:24].[CH2:26](Br)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CS(C)=O>[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][N:4]1[C:23]([S:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[S:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6348Carbon DisulfideHCID 81011-BromohexaneHCID 8471TriethylamineHCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Produkt 1

HCID 13392981n-Hexyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Versuchsvorschrift

(3S)-3-Hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (2.02 g) is dissolved in dimethylsulfoxide (10 ml), and thereto are added triethylamine (1.67 ml) and CS2 (0.72 ml), and the mixture is stirred at room temperature for 20 minutes. To the reaction mixture is added dropwise n-hexyl bromide (1.98 g), and the mixture is stirred at room temperature for 2.5 hours. The reaction mixture is poured onto ice-water and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried over sodium sulfate, and then distilled to remove the solvent. The residue is recrystallized from ether-n-hexane to give the title compound (2.65 g, 73.2%) as colorless needles, m.p. 102°-106° C. NMR (CDCl3, δ): 0.90 (broad, t, 3H, --(CH2)5 --CH3); Mass m/e: 362 (M+), 244 (M+ --C6H13SH); [α]D20 +130.0° (c=1.0, methanol).

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 2.5 hours
  2. additionThe reaction mixture is poured onto ice-water
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe ethyl acetate layer is washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue is recrystallized from ether-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-537bca8a081e45dbbc8a50af57fc05e0
Quelldatensatz
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04612317

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion