Carbon Disulfide → HCID 13375551, compound

HRID 65065Notes

Reaction equation

HRID 65065 reaction equation
[OH:1][CH2:2][CH2:3][C@H:4]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH2:6][NH:5]1.[OH-].[Na+].[C:19](=[S:21])=[S:20].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1>C(OCC)(=O)C.C(O)C>[OH:1][CH2:2][CH2:3][C@H:4]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH2:6][N:5]1[C:19]([S:21][CH2:27][C:26]1[CH:29]=[CH:30][C:23]([Cl:22])=[CH:24][CH:25]=1)=[S:20]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 13863924HCID 13863924, compound

Product 1

HCID 13375551HCID 13375551, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In the same manner as described in Example 13 by using (3R)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydro-β-carboline (100 mg), 2N NaOH (0.23 ml), CS2 (0.028 ml), 4-chlorobenzyl chloride (82 mg) and 70% ethanol (2.5 ml), there is prepared the title compound (66 mg, 34%) as white powder, [α]D20 -115.8° (c=1.0, ethyl acetate). Mass m/e: 416 (M+), 258 (M+ --p--Cl--C6H4 --CH2SH).

Sources & evidence

ORD record
ord-c9da69fba55d41bd81f2e1894fd58568
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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