Ethyl Acetate → HCID 18670519, compound

HRID 1059376Notes

Reaction equation

HRID 1059376 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].[Cl:14][C:15]1[C:20](Cl)=[N:19][CH:18]=[CH:17][N:16]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10])[C:20]1[C:15]([Cl:14])=[N:16][CH:17]=[CH:18][N:19]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 69157Benzenamine, N-methyl-2-nitro-HCID 785752,3-Dichloropyrazine

Product 1

HCID 18670519HCID 18670519, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.52 g of N-methyl-2-nitroaniline in N,N-dimethylformamide (50 ml) was added in a nitrogen atmosphere 0.44 g of sodium hydride. After stirring for 30 minutes, 1.75 g of 2,3-dichloropyrazine was added thereto and the resulting mixture was stirred at room temperature for additional 6 hours. Then the reaction mixture was distributed into ethyl acetate and a saturated aqueous solution of sodium dihydrogenphosphate and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed successively with water and a saturated aqueous solution of sodium chloride and 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 0.586 g of the title compound as an oily substance.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for additional 6 hours
  2. extractiona saturated aqueous solution of sodium dihydrogenphosphate and the aqueous layer was extracted with ethyl acetate
  3. washwashed successively with water
  4. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ae513f77cb1e46a68e725cab20f18340
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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