Sodium Methoxide → HCID 15434937, compound

HRID 1604305Notes

Reaction equation

HRID 1604305 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[N:13]=[C:12](Cl)[CH:11]=[N:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:17][O-:18].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[N:13]=[C:12]([O:18][CH3:17])[CH:11]=[N:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 15434936HCID 15434936, compound

Product 1

HCID 15434937HCID 15434937, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF was dissolved 2.77 g of 2-(3,5-dichlorophenyl)-5-chloro-2,3-dihydro-1,2,4-triazin-3-one followed by addition of sodium methoxide in an equimolar amount to the starting compound, and the mixture was stirred at room temperature for 1 hour. After completion of this reaction, the reaction mixture was concentrated under reduced pressure and ice-water was added to the residue. The resulting crystals were collected by filtration, dried and dissolved in 100 ml of chloroform. The chloroform solution was dried over anhydrous magnesium sulfate, concentrated and purified by column chromatography (Merck Silica Gel 60; dichloromethane-methanol=10:1) to provide 0.4 g of white crystals (m.p. 164° C.).

Workup

  1. customAfter completion of this reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure and ice-water
  3. additionwas added to the residue
  4. filtrationThe resulting crystals were collected by filtration
  5. customdried
  6. dissolutiondissolved in 100 ml of chloroform
  7. dry with materialThe chloroform solution was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by column chromatography (Merck Silica Gel 60; dichloromethane-methanol=10:1)

Sources & evidence

ORD record
ord-42d1e7055c1f44c4a47fb4d328af484f
Source dataset
uspto-grants-1999_11
Patent number
US05994355

Reaction notes

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