Carbon Disulfide → (3RS)-2-[(Phenethylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

HRID 1249055Notes

Reaction equation

HRID 1249055 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[K+].[C:19](=[S:21])=[S:20].[CH2:22](Br)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.CS(C)=O>[CH2:22]([S:20][C:19]([N:2]1[CH:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)=[S:21])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 7666Phenethyl bromideHCID 14797Potassium HydroxideHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 13561956(3RS)-2-[(Phenethylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

In the same manner as descsribed in Example 32, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (3.24 g), KOH (1.75 g), carbon disulfide (0.91 ml), dimethylsulfoxide (20 ml), water (5 ml) and phenethyl bromide (3.33 g) are reacted and treated. The product is crystallized from chloroform to give the title compound (2.77 g), m.p. 89°-90° C.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product is crystallized from chloroform

Sources & evidence

ORD record
ord-92c18c19ff1447fbb803e7be3664e4e6
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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