Carbon Disulfide → 4-Methoxybenzyl (3RS)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65071Notes

Reaction equation

HRID 65071 reaction equation
[OH:1][CH2:2][CH: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(CC)CC)C.[C:23](=[S:25])=[S:24].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1>CS(C)=O>[OH:1][CH2:2][CH: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][CH2:32][C:31]1[CH:34]=[CH:35][C:28]([O:27][CH3:26])=[CH:29][CH:30]=1)=[S:24]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 13375505{1H,2H,3H,4H,9H-pyrido[3,4-b]indol-3-yl}methanol

Product 1

HCID 138590474-Methoxybenzyl (3RS)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as described in Example 29 by using (3RS)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (1.01 g), triethylamine (0.7 ml), CS2 (0.3 ml), 4-methoxybenzyl chloride (1.0 g) and dimethylsulfoxide (5 ml), there is prepared the title compound (1.41 g, 71%) as white powder, NMR (CDCl3 +DMSO-d6, δ): 4.52 (s, 2H, ##STR16## Mass m/e: 398 (M+), 244 (M+ -- ##STR17##

Sources & evidence

ORD record
ord-eb7cdabd6ecb42389b6cd87ae29973cd
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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