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Iodoethane → Ethyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65047
Notes
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Reaction equation

HRID 65047 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([CH2:21][CH3:22])CC)C.[C:23](=[S:25])=[S:24].C(I)C>O.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:23]([S:25][CH2:21][CH3:22])=[S:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 13375515Ethyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

In the same manner as described in Example 2 by using (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (2.02 g), triethylamine (1.52 g), CS2 (1.14 g), ethyl iodide (2.34 g), ethanol (25 ml) and water (5 ml), there is prepared the title compound (2.0 g, 65%) as colorless needles, m.p. 74°-76° C. (recrystallized from ethanol), [α]D20 +146.0° (c=1, methanol). NMR (CDCl3, δ): 1.35 (t, J=7.5 Hz, 3H, CSSCH2CH3), 3.36 (q, J=7.5 Hz, 2H, CSSCH2CH3), Mass m/e: 306 (M+), 244 (M+ -thioethanol).

Workup

  1. customis prepared
  2. customthe title compound (2.0 g, 65%) as colorless needles, m.p. 74°-76° C. (recrystallized from ethanol), [α]D20 +146.0° (c=1, methanol)

Sources & evidence

ORD record
ord-73a28dd769494e7bac2a6f11d1eeb7ea
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04612317

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes