Methyl iodide → Methyl (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65072

Reaction equation

HRID 65072 reaction equation
[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[C@H:5]([CH3:16])[NH:4]1.[C:17](=[S:19])=[S:18].[CH2:20](N(CC)CC)C.CI>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[C@H:5]([CH3:16])[N:4]1[C:17]([S:19][CH3:20])=[S:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 13375562(1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 13375530Methyl (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(1RS, 3RS)-cis-3-Hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (4.326 g) is dissolved in dimethylsulfoxide (20 ml), and thereto are added CS2 (2.4 ml) and triethylamine (5.6 ml). The mixture is stirred at room temperature for 30 minutes, and thereto is added dropwise methyl iodide (2.5 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, 5% HCl and water in order, dried over sodium sulfate and then distilled to remove the solvent. The residue is recrystallized from aqueous ethanol to give the title compound (5.5 g, 90%) as colorless needles, m.p. 164°-166° C., NMR (CDCl3, δ): 1.68 (d, J=6.8 Hz, 3H, C1 --CH3), 2.73 (s, 3H, CSSCH3); Mass m/e: 306 (M+), 258 (M+ --CH 3 SH).

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% HCl and water in order
  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-332c494c01eb42aa973a21aa6f49dcd1
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Linked notes

Loading…