Dimethyl Sulfoxide → HCID 59351413, compound

HRID 2191937Notes

Reaction equation

HRID 2191937 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-5bbe61f100664f2f94b5959d160b2dca
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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