Carbon Disulfide → HCID 13561939, compound

HRID 1249046Notes

Reaction equation

HRID 1249046 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].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CS(C)=O>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][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])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic AcidHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 13561939HCID 13561939, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as described in Example 16, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (4.32 g), 10N NaOH (4 ml), carbon disulfide (1.4 ml), dimethylsulfoxide (20 ml) and 4-methoxybenzyl bromide (4.02 g) are reacted and treated. The product is crystallized from isopropyl ether to give the title compound (6.50 g, 79%) as colorless needles, m.p. 195°-196° C.

Workup

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

Sources & evidence

ORD record
ord-be7db92f534844cd9321ce37b73d5ce3
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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