Ethanol → (3RS)-2-[(n-Butylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

HRID 1249030Notes

Reaction equation

HRID 1249030 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(O)C.[CH2:22](I)[CH2:23][CH2:24][CH3:25].[C:27](=[S:29])=[S:28]>>[CH2:22]([S:29][C:27]([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:28])[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 5

HCID 702EthanolHCID 6348Carbon DisulfideHCID 10962Butyl iodideHCID 14797Potassium HydroxideHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 13561924(3RS)-2-[(n-Butylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

Procedure

In the same manner as described in Example 6, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (3.24 g), KOH (96%, 1.75 g), 50% ethanol (65 ml), carbon disulfide (0.91 ml) and n-butyl iodide (3.3 g) are reacted and treated. The product is crystallized from chloroform to give the title compound (1.9 g) as pale yellow crystals, m.p. 163°-164° C.

Workup

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

Sources & evidence

ORD record
ord-eadd99cbbc9c4f758ed6387d76fa90a4
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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