Methyl iodide → HCID 86741129, compound

HRID 1732128Notes

Reaction equation

HRID 1732128 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[CH2:11][NH:10][C@H:9]([C:15]([O:17]C)=[O:16])[CH2:8][C:7]2=1.[OH-].[Na+].[C:21](=[S:23])=[S:22].[CH3:24]I>CO>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[CH2:11][N:10]([C:21]([S:23][CH3:24])=[S:22])[C@H:9]([C:15]([OH:17])=[O:16])[CH2:8][C:7]2=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14798Sodium Hydroxide2×HCID 13653080HCID 13653080, compound

Product 1

HCID 86741129HCID 86741129, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

610 mg of methyl (3S)-8-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate are dissolved in 20 ml of methanol, and 2 ml of a 10% aqueous sodium hydroxide solution are added thereto. The mixture is stirred at room temperature for 3 hours. One ml of a 10% aqueous sodium hydroxide solution and 228 mg of carbon disulfide are added to the mixture, and the mixture is stirred at room temperature for 30 minutes. Then, 355 mg of methyl iodide are adde to the mixture, and the mixture is stirred at the same temperature for 2.5 hours. After the reaction, the mixture is evaporated to remove the solvent. The residue is dissolved in water, and the aqueous solution is extracted with ethyl acetate. The aqueous layer is acidified with 10% HCl, and then extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove the solvent. A mixture of ether and n-hexane is added to the residue, and the precipitates are collected. 200 mg of (3S)-8 -methyl-2-(methylthio)thiocarbonyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid are obtained as white powder.

Workup

  1. stirringthe mixture is stirred at room temperature for 30 minutes
  2. stirringthe mixture is stirred at the same temperature for 2.5 hours
  3. customAfter the reaction
  4. customthe mixture is evaporated
  5. customto remove the solvent
  6. dissolutionThe residue is dissolved in water
  7. extractionthe aqueous solution is extracted with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washThe extract is washed with water
  10. customdried
  11. customevaporated
  12. customto remove the solvent
  13. additionA mixture of ether and n-hexane
  14. additionis added to the residue
  15. customthe precipitates are collected

Sources & evidence

ORD record
ord-01af04b662e947acb4c8e7894299a174
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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