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

HRID 65077Notes

Reaction equation

HRID 65077 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-abb64ae05e0b47a79a5cdf6d6a9f60d8
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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