Carbon Disulfide → Methyl (3RS)-9-methyl-2-[(2-thenylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

HRID 1249078Notes

Reaction equation

HRID 1249078 reaction equation
[CH3:1][N:2]1[C:14]2[CH2:13][NH:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.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>CO>[CH3:1][N:2]1[C:14]2[CH2:13][N:12]([C:26]([S:28][CH2:34][C:29]3[S:33][CH:32]=[CH:31][CH:30]=3)=[S:27])[CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 698302-(Chloromethyl)thiopheneHCID 12789147methyl (3RS)-9-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

Product 1

HCID 13561991Methyl (3RS)-9-methyl-2-[(2-thenylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylateYield 57.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the same manner as described in Example 53, methyl (3RS)-9-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (421 mg), triethylamine (365 mg), carbon disulfide (137 mg), methanol (20 ml) and 2-thenyl chloride (238 mg) are reacted and treated. The product is recrystallized from methanol to give the title compound (360 mg, 57.6%) as colorless prisms, m.p. 139°-140° C.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product is recrystallized from methanol

Sources & evidence

ORD record
ord-0a672be6ae5b486d8968a04da98745d0
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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