2-Methoxyethanol → HCID 86616974, compound

HRID 1865889Notes

Reaction equation

HRID 1865889 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Br[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[N:13][C:12]([Br:23])=[CH:11][N:10]=1.CCCCCCC>CS(C)=O.ClCCl>[Br:23][C:12]1[N:13]=[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C:9]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:10][CH:11]=1

Participants

7

Reactant 4

HCID 80192-MethoxyethanolHCID 8900HeptaneHCID 24758Sodium hydrideHCID 86616975HCID 86616975, compound

Product 1

HCID 86616974HCID 86616974, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.077 g (0.001 mol) 2-methoxyethanol in 2 ml dimethylsulfoxide was added at room temperature 0.088 g (0.002 mol) sodium hydride (55% in oil) and the mixture was stirred at room temperature for 1 h. To the resulting solution was added 0.352 g 2,5-dibromo-3-(2,4-dichloro-phenyl)-pyrazine and the mixture was stirred at room temperature for 3 h. The resulting reaction mixture was partitioned between water and ethyl acetate, the phases were separated and the organic phase washed twice with water, dried with sodium sulfate and evaporated. The residue was purified by chromatography on silica gel using dichloromethane:heptane=3:1 to dichloromethane as eluent to yield 0.090 g (24% yield) of the title compound as the faster eluting compound as white crystals melting at 92-93° C. and 0.171 g (45% yield) of its isomer 2-bromo-3-(2,4-dichloro-phenyl)-5-(2-methoxy-ethoxy)-pyrazine as the slower eluting compound as yellowish oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 h
  2. customThe resulting reaction mixture
  3. customwas partitioned between water and ethyl acetate
  4. customthe phases were separated
  5. washthe organic phase washed twice with water
  6. dry with materialdried with sodium sulfate
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1070723c87a3444293679aa12ecbec15
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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