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

HRID 1249077Notes

Reaction equation

HRID 1249077 reaction equation
Cl.[CH3:2][N:3]1[C:15]2[CH2:14][NH:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.C(N(CC)CC)C.[C:27](=[S:29])=[S:28].[CH3:30]I>CO>[CH3:2][N:3]1[C:15]2[CH2:14][N:13]([C:27]([S:29][CH3:30])=[S:28])[CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 12789148methyl (3RS)-9-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate hydrochloride

Product 1

HCID 13561990Methyl (3RS)-9-methyl-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylateYield 80.5%

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 hydrochloride (5.61 g), triethylamine (4.86 g), carbon disulfide (1.83 g), methanol (200 ml) and methyl iodide (3.40 g) are reacted and treated. The product is recrystallized from methanol to give the title compound (5.38 g, 80.5%) as colorless needles, m.p. 170°-171° C.

Workup

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

Sources & evidence

ORD record
ord-5354f84231114e82b410cefd29cafa89
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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