Dimethyl Sulfoxide → HCID 59351413, compound

HRID 555812Notes

Reaction equation

HRID 555812 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:11].[Cl:19][C:20]1[C:25](Cl)=[N:24][CH:23]=[CH:22][N:21]=1.CS(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:25]2[C:20]([Cl:19])=[N:21][CH:22]=[CH:23][N:24]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 785752,3-DichloropyrazineHCID 9859873HCID 9859873, compound

Product 1

HCID 59351413HCID 59351413, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

In 250 mL round bottom flask were charged benzo[d]thiazol-2-yl(4-hydroxyphenyl)methanone (6.0 g, 23.5 mmol), 2,3-dichloro-pyrazine (3.48 g, 23.5 mmol), DMSO (60 mL), and cesium carbonate (15 g, 47 mmol). The reaction mixture was stirred at 90° C. for 6 h. The reaction mixture was diluted with cold water and the precipitate was collected by filtration. The crude product was purified by silica gel column chromatography with hexane and ethyl acetate to give the title compound. [M+H]=368.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customThe crude product was purified by silica gel column chromatography with hexane and ethyl acetate

Sources & evidence

ORD record
ord-bdc2c7eb101343bbae9220e05a307ca4
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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