Ethyl Acetate → HCID 18670174, compound

HRID 1059296Notes

Reaction equation

HRID 1059296 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[C:5](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[C:29](Cl)=[N:28][CH:27]=[CH:26][N:25]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:16][O:15][C:4]1[CH:3]=[C:2]([S:1][C:29]2[C:24]([Cl:23])=[N:25][CH:26]=[CH:27][N:28]=2)[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 785752,3-DichloropyrazineHCID 18670273HCID 18670273, compound

Product 1

HCID 18670174HCID 18670174, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.45 g of methyl 4-mercapto-5-nitro-o-anisate in N,N-dimethylformamide (100 ml) were added 4.4 g of potassium carbonate and 4.75 g of 2,3-dichloropyrazine. Then the mixture was allowed to react at 80° C. for 2 hours. After adding ethyl acetate, the reaction mixture was washed with a saturated aqueous solution of sodium chloride and the organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 3.14 g of the title compound as a brown solid.

Workup

  1. customto react at 80° C. for 2 hours
  2. washthe reaction mixture was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-69ea93aa12384167948431391bd7dc1b
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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