Sulfur → HCID 13505212, compound

HRID 1731746Notes

Reaction equation

HRID 1731746 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([CH:20]1[CH2:25][CH2:24][CH:23]=[CH:22][CH2:21]1)=[CH:13][CH:12]=3)=[O:5])[CH3:2].[S]>CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5362487SulfurHCID 13505188HCID 13505188, compound

Product 1

HCID 13505212HCID 13505212, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

435 mg (1.3 mmol) of 6-(1-cyclohexen-4-yl)-4-methyl-β-carboline-3-carboxylic acid ethyl ester is heated in 10 ml of dimethyl sulfoxide with 125 mg of sulfur under nitrogen for 2 hours to 180° C. After evaporation under vacuum, the reaction mixture is distributed in methylene chloride/saturated sodium bicarbonate solution. The methylene chloride phase is evaporated and the residue chromatographed over silica gel with toluene:glacial acetic acid:water=10:10:1 as the eluent. After evaporation of the corresponding fractions and mixing with hexane under agitation, 48 mg (8.4% of theory) of 6-phenyl-4-methyl-β-carboline-3-carboxylic acid ethyl ester is obtained, mp 241°-242° C.

Workup

  1. customAfter evaporation under vacuum
  2. customThe methylene chloride phase is evaporated
  3. customthe residue chromatographed over silica gel with toluene
  4. customAfter evaporation of the corresponding fractions
  5. additionmixing with hexane under agitation

Sources & evidence

ORD record
ord-f9e3cbe98b5a4b2a835975bf879c36fa
Source dataset
uspto-grants-1986_11
Patent number
US04623649

Reaction notes

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