Iodoethane → Ethyl (1RS, 3SR)-trans-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 65077
[CH2:1]([C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@H:5]([CH2:16][OH:17])[NH:4]1)[CH3:2].[C:18](=[S:20])=[S:19].[CH2:21](N(CC)CC)[CH3:22].C(I)C>CS(C)=O>[CH2:1]([C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@H:5]([CH2:16][OH:17])[N:4]1[C:18]([S:20][CH2:21][CH3:22])=[S:19])[CH3:2]

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 86741006(1RS, 3SR)-trans-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Produkt 1

HCID 86741017Ethyl (1RS, 3SR)-trans-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

(1RS, 3SR)-trans-1-Ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (0.461 g) is dissolved in dimethylsulfoxide (2 ml), and thereto are added CS2 (0.27 ml) and triethylamine (0.61 ml). The mixture is stirred at room temperature for one hour, and thereto is added dropwise ethyl iodide (0.38 ml), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is poured onto ice-water, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate and then distilled to remove the solvent. The residue is recrystallized from aqueous ethanol to give the title compound (0.477 g, 71%) as colorless needles, m.p. 82°-84° C., NMR (CDCl3, δ): 1.40 (t, J=7.0 Hz, 3H, CSSCH2CH3); Mass m/e: 334 (M+), 272 (M+ --CH3CH2SH).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-abb64ae05e0b47a79a5cdf6d6a9f60d8
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612317

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