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

HRID 1249051Notes

Reaction equation

HRID 1249051 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-].[Na+].[C:19](=[S:21])=[S:20].[C:22]1([CH2:27]Cl)[S:26][CH:25]=[CH:24][CH:23]=1>CS(C)=O>[C:22]1([CH2:27][S:20][C:19]([N:2]2[CH:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[S:21])[S:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 698302-(Chloromethyl)thiopheneHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 13561949(3RS)-2-[(2-Thenylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as descsribed in Example 32, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (4.32 g), 20N NaOH (2.2 ml), carbon disulfide (1.45 ml), dimethylsulfoxide (13 ml) and 2-thenyl chloride (3.18 g) are reacted and treated. The product is crystallized from ethanol to give the title compound (4.1 g) as pale yellow crystals, m.p. 172° C. (decomp.).

Workup

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

Sources & evidence

ORD record
ord-b0354dd1e0aa4b55bce453789fe4707f
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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