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Carbon Disulfide → Ethyl (3R)-2-[(2-thenylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

HRID 1249071
Notes
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Reaction equation

HRID 1249071 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][C@H:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:2]1.C(N(CC)CC)C.[C:26](=[S:28])=[S:27].[C:29]1([CH2:34]Cl)[S:33][CH:32]=[CH:31][CH:30]=1>C(O)C>[C:29]1([CH2:34][S:27][C:26]([N:2]2[C@@H:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[S:28])[S:33][CH:32]=[CH:31][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 698302-(Chloromethyl)thiopheneHCID 7223904ethyl (3R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate

Product 1

HCID 13561985Ethyl (3R)-2-[(2-thenylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same manner as described in Example 53, ethyl (3R)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (2.24 g), triethylamine (1.25 g), carbon disulfide (0.76 ml), ethanol (50 ml) and 2-thenyl chloride (1.65 g) are reacted and treated. The product is recrystallized from ethyl acetate-n-hexane to give the title compound (2.60 g, 63%) as colorless needles, m.p. 205°-207° C.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-8dcd5b74adb34f58997957697edbd9fe
Source dataset
uspto-grants-1986_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04628057

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes