Carbon Disulfide → Sodium (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65044Notes

Reaction equation

HRID 65044 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][NH:4]1.[C:16](=[S:18])=[S:17].[OH-].[Na+:20]>C(O)C>[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][N:4]1[C:16]([S-:18])=[S:17].[Na+:20]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 23701790Sodium (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (5.06 g), CS2 (2.0 g) and ethanol (230 ml) is added dropwise a 1N NaOH solution (25 ml) at room temperature. The mixture is stirred for 2 hours, and thereto is added ethanol. The precipitated crystals are collected by filtration and recrystallized from water-ethanol to give the title compound (5.3 g, 71%) as colorless needles, m.p. 209°-210° C. (decomp.), [α]D20 +151.8° (c=1, methanol).

Workup

  1. filtrationThe precipitated crystals are collected by filtration
  2. customrecrystallized from water-ethanol

Sources & evidence

ORD record
ord-68a92624f9b6419bb6a8c8c541a64b92
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

Loading…