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

HRID 1249073Notes

Reaction equation

HRID 1249073 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].[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1>C(O)C>[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([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])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8471TriethylamineHCID 7223904ethyl (3R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate

Product 1

HCID 13561988Ethyl (3R)-2-[(4-chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylateYield 69%

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 (2.00 g), triethylamine (1.07 g), carbon disulfide (0.65 ml), ethanol (60 ml) and 4-chlorobenzyl chloride (1.72 g) are reacted and treated. The product is recrystallized from ethyl acetate-n-hexane to give the title compound (2.75 g, 69%) as pale yellow needles, m.p. 198°-199° C.

Workup

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

Sources & evidence

ORD record
ord-d7154dcda432448e955fb0b290b0d57a
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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