Sodium hydrosulfide → Bis-(6,7-dichloro-2-isopropylquinoxalin-3-yl)sulfide

HRID 584649Notes

Reaction equation

HRID 584649 reaction equation
Cl[C:2]1[C:11]([CH:12]([CH3:14])[CH3:13])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:16])=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.[SH-:17].[Na+]>CN(C=O)C>[Cl:16][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][C:7]=1[Cl:15])[N:10]=[C:11]([CH:12]([CH3:14])[CH3:13])[C:2]([S:17][C:2]1[C:11]([CH:12]([CH3:14])[CH3:13])=[N:10][C:9]3[C:4]([N:3]=1)=[CH:5][C:6]([Cl:16])=[C:7]([Cl:15])[CH:8]=3)=[N:3]2

Participants

4

Reactant 2

HCID 28015Sodium hydrosulfideHCID 223410512,6,7-Trichloro-3-isopropylquinoxaline

Product 1

HCID 9871050Bis-(6,7-dichloro-2-isopropylquinoxalin-3-yl)sulfideYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

To a solution of 2,6,7-trichloro-3-isopropylquinoxaline (105 mg, 0.38 mmol) in DMF (3 ml) was added sodium hydrosulfide (21 mg, 0.23 mmol). The reaction mixture was stirred at 55-60° C. in an oil bath overnight. The product was purified by a plug filtration through silica gel using ethyl acetate:hexanes 1:20 followed by preparative thin layer chromatography using ethyl acetate:hexanes 1:60. Extraction of the product band using chloroform afforded the title compound as a white solid in 20% yield.

Workup

  1. filtrationThe product was purified by a plug filtration through silica gel
  2. extractionExtraction of the product band

Sources & evidence

ORD record
ord-e1e3080c157941678c5d4a7aaf59fb2b
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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