Methyl iodide → Methyl (3RS)-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

HRID 1249066

Reaction equation

HRID 1249066 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3]([C:14]([O:16][CH3:17])=[O:15])[NH:2]1.C(N(CC)CC)C.[C:25](=[S:27])=[S:26].[CH3:28]I>CO>[CH3:28][S:26][C:25]([N:2]1[CH:3]([C:14]([O:16][CH3:17])=[O:15])[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)=[S:27]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 1777282,3,4,9-Tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester

Product 1

HCID 13561978Methyl (3RS)-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylateYield 65.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (2.30 g) is dissolved in methanol (50 ml) and thereto are added triethylamine (1.21 g) and carbon disulfide (920 mg). The mixture is stirred at room temperature for 20 minutes and thereto is added dropwise methyl iodide (1.70 g). The mixture is stirred for 4 hours and distilled under reduced pressure to remove the solvent. The residue is dissolved in ethyl acetate, and the mixture is washed with water, dried and distilled to remove the solvent. The residue is recrystallized from ether-n-hexane to give the title compound (2.10 g, 65.6%) as colorless needles, m.p. 132°-134° C.

Workup

  1. stirringThe mixture is stirred for 4 hours
  2. distillationdistilled under reduced pressure
  3. customto remove the solvent
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washthe mixture is washed with water
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is recrystallized from ether-n-hexane

Sources & evidence

ORD record
ord-836bbc67d48f436686a50a33da215470
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Linked notes

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