Dimethyl Sulfoxide → HCID 13561962, compound

HRID 1249058Notes

Reaction equation

HRID 1249058 reaction equation
[CH3:1][C@H: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]([C:15]([OH:17])=[O:16])[NH:3]1.[OH-].[Na+].[CH3:20][S:21]([CH3:23])=O.CI.C(=S)=[S:27]>O>[CH3:1][C@H: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]([C:15]([OH:17])=[O:16])[N:3]1[C:20]([S:21][CH3:23])=[S:27]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 1483851H-Pyrido(3,4-b)indole-3-carboxylic acid, 2,3,4,9-tetrahydro-1-methyl-, cis-

Product 1

HCID 13561962HCID 13561962, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2.30 g), 10N NaOH (2 ml) and dimethylsulfoxide (6 ml) is added dropwise carbon disulfide (912 mg) and further added dropwise methyl iodide (1.7 g) at 0° C. The mixture is stirred at room temperature for one hour, and to the mixture is added water, and then extracted with ethyl acetate. The aqueous layer is acidified with 10% HCl and extracted with ethyl acetate. The extract is dried and distilled to remove the solvent. The residue is crystallized from chloroform to give the title compound (1.59 g, 50%) as colorless needles, m.p. 134°-137° C. (decomp.).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. customThe extract is dried
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue is crystallized from chloroform

Sources & evidence

ORD record
ord-d1ee7a3a8b044b198bd36db2e07546a6
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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