Methyl iodide → HCID 13711356, compound

HRID 1732129Notes

Reaction equation

HRID 1732129 reaction equation
Cl.[CH2:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][C@@H:4]([CH2:15][C:16]([OH:18])=[O:17])[NH:3]1.C(N(CC)CC)C.[C:26](=[S:28])=[S:27].[CH3:29]I>CS(C)=O>[CH3:29][S:27][C:26]([N:3]1[C@H:4]([CH2:15][C:16]([OH:18])=[O:17])[CH2:5][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:13][C:14]=2[CH2:2]1)=[S:28]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 13711372HCID 13711372, compound

Product 1

HCID 13711356HCID 13711356, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

235 mg of (3S)-1,2,3,4-tetrahydro-β-carboline-3-acetic acid hydrochloride are dissolved in 2 ml of dimethylsulfoxide. 0.42 ml of triethylamine and 0.07 ml of carbon disulfide are added to the mixture, and the mixture is stirred at room temperature for 30 minutes. Then, 0.07 ml of methyl iodide are added dropwise to the mixture. The mixture is further stirred at the same temperature for 2 hours. The reaction mixture is evaporated to remove the solvent, and the residue is dissolved in water. The aqueous solution is acidified with 5% HCl, and extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove the solvent. Aqueous ethanol is added to the residue, and the precipitates are collected. 102 mg of (3S)-2-(methylthio)thiocarbonyl-1,2,3,4-tetrahydro-β-carboline-3-acetic acid are obtained as white powder.

Workup

  1. stirringThe mixture is further stirred at the same temperature for 2 hours
  2. customThe reaction mixture is evaporated
  3. customto remove the solvent
  4. dissolutionthe residue is dissolved in water
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with water
  7. customdried
  8. customevaporated
  9. customto remove the solvent
  10. additionAqueous ethanol is added to the residue
  11. customthe precipitates are collected

Sources & evidence

ORD record
ord-f7bc97c9b60049afa742cc07970a60f4
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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