Sodium hydride → HCID 18670155, compound

HRID 1059380Notes

Reaction equation

HRID 1059380 reaction equation
[CH3:1][C:2]1[C:7]([SH:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:15]1[C:16]([Cl:21])=[N:17][CH:18]=[CH:19][N:20]=1.P([O-])(O)(O)=O.[Na+]>O1CCCC1>[CH3:1][C:2]1[C:7]([S:8][C:15]2[C:16]([Cl:21])=[N:17][CH:18]=[CH:19][N:20]=2)=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 785752,3-DichloropyrazineHCID 10442104HCID 10442104, compoundHCID 23672064Monosodium phosphate

Product 1

HCID 18670155HCID 18670155, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.254 g of 6-methyl-2-nitrobenzenethiol in tetrahydrofuran (10 ml) was added 0.326 g of sodium hydride under ice-cooling in a nitrogen atmosphere. After stirring for 10 minutes, 1.67 g of dichloropyrazine was added thereto and the resulting mixture was stirred at room temperature for 1 hour and heated under reflux for 1.5 hour. Then the reaction mixture was poured into a saturated aqueous solution of sodium dihydrogenphosphate and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure. Then the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 0.737 g of the title compound as a red oily substance.

Workup

  1. temperaturecooling in a nitrogen atmosphere
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. temperatureheated
  4. temperatureunder reflux for 1.5 hour
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customThen the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c6f8f82d5569450ea7f5f3be26089ac7
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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