Carbon Disulfide → HCID 13561940, compound

HRID 1249047Notes

Reaction equation

HRID 1249047 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].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23]>CS(C)=O>[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29][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:27][CH:26]=1)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 660114-Nitrobenzyl bromideHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 13561940HCID 13561940, compoundYield 54%

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 (4.22 g), 10N NaOH (3.9 ml), carbon disulfide (1.4 ml), dimethylsulfoxide (12 ml) and 4-nitrobenzyl bromide (4.63 g) are reacted and treated. The product is crystallized from ethanol to give the title compound (4.7 g, 54%) as yellow crystals, m.p. 194°-195° C.

Workup

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

Sources & evidence

ORD record
ord-66b7b17879ad4379be31e336188b4650
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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