Hydrochloric Acid → (3S)-3-Hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioic acid

HRID 65066Notes

Reaction equation

HRID 65066 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(N(CC)CC)C.[C:23](=[S:25])=[S:24].Cl>CS(C)=O>[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:23]([SH:25])=[S:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 13375513(3S)-3-Hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioic acidYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(3S)-3-Hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (2.02 g) is dissolved in dimethylsulfoxide (10 ml), and thereto are added triethylamine (1.67 ml) and CS2 (0.72 ml), and the mixture is stirred at room temperature for 3 hours. The reaction mixture is poured onto ice-water and is neutralized with 10% HCl. The precipitated crystals are collected by filtration, washed with water and then recrystallized from methanol to give the title compound (1.46 g, 60%) as colorless needles, m.p. 225°-227° C. IR νmaxNujol (cm-1): 3480, 3340; Mass m/e: 278 (M+), 244 (M+ --H2S); [α]D20 +170.0° (c=1.0, methanol).

Workup

  1. additionThe reaction mixture is poured onto ice-water
  2. filtrationThe precipitated crystals are collected by filtration
  3. washwashed with water
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-28574f1eae204b4ea67f3c62482193c7
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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