Carbon Disulfide → HCID 13375525, compound

HRID 65050Notes

Reaction equation

HRID 65050 reaction equation
[OH:1][CH2:2][C@H: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.[OH-].[K+].[C:18](=[S:20])=[S:19].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CO.C(O)C>[OH:1][CH2:2][C@H: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:18]([S:20][CH2:26][C:25]1[CH:28]=[CH:29][C:22]([Cl:21])=[CH:23][CH:24]=1)=[S:19]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14797Potassium HydroxideHCID 13375507(3R)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 13375525HCID 13375525, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

In the same manner as described in Example 8 by using (3R)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (1.01 g), 2N KOH (2.5 ml), CS2 (0.3 ml), 4-chlorobenzyl chloride (0.81 g) and 70% ethanol (20 ml), there is prepared the title compound (1.34 g, 67%) as white powder, [α]D20 -111.8° (c=1.0, methanol). NMR (CDCl3 -DMSO-d6, δ): 4.56 (s, 2H, CSSCH2C6H4 -p-Cl), Mass m/e: 402 (M+), 244 (M+ -p-Cl-C6H4CH2SH).

Sources & evidence

ORD record
ord-f008ead447c74e179fc8d7c2b9692401
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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