Dimethyl Sulfoxide → HCID 13561928, compound

HRID 1249036Notes

Reaction equation

HRID 1249036 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+].CS(C)=O.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].[C:30](=[S:32])=[S:31]>>[CH2:28]([O:27][C:25]([CH2:24][S:32][C:30]([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:31])=[O:26])[CH3:29]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6348Carbon DisulfideHCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 13561928HCID 13561928, compoundYield 65%

Procedure

In the same manner as described in Example 6, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2.16 g), 10N NaOH (2 ml), dimethylsulfoxide (6 ml), carbon disulfide (912 mg) and ethyl bromoacetate (2.0 g) are reacted. The product is recrystallized from ethanol to give the title compound (1.41 g, 65%) as colorless needles, m.p. 190°-192° C.

Workup

  1. customare reacted
  2. customThe product is recrystallized from ethanol

Sources & evidence

ORD record
ord-c2b9e047f0b14946ac5504339c8a0d56
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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