Water → HCID 19770559, compound

HRID 1589713Notes

Reaction equation

HRID 1589713 reaction equation
[CH3:1][O-:2].[Na+].[N:4]1([CH:9](Cl)[CH:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH2:11][CH3:12])[CH:8]=[N:7][CH:6]=[N:5]1.O>CO.[I-].[K+]>[N:4]1([CH:9]([O:2][CH3:1])[CH:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH2:11][CH3:12])[CH:8]=[N:7][CH:6]=[N:5]1

Participants

6

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 14552049HCID 14552049, compound

Product 1

HCID 19770559HCID 19770559, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 887MethanolSolvent

Procedure

9.4 g of sodium methylate and 0.2 g of potassium iodide are added to a solution of 26.6 g of 1-(1,2,4-triazol-1-yl)-1-chloro-2-(2,4-dichlorophenyl)-butane in 200 ml of methanol. The reaction mixture is refluxed for 48 hours, after which 100 ml of water are added to the solution and the mixture is extracted several times with methyl tert-butyl ether. The organic phase isolated is washed twice with water, then dried over sodium sulfate and evaporated down and the remaining residue is purified by chromatography over silica gel (9:1 ethyl acetate/n-hexane). 6.2 g (24%) of 1-(1,2,4-triazol-1-yl)-1-methoxy-2-(2,4-dichlorophenyl)-butane are obtained as a 1:1 diastereomer mixture [compound No. 1).

Workup

  1. temperatureThe reaction mixture is refluxed for 48 hours
  2. extractionthe mixture is extracted several times with methyl tert-butyl ether
  3. customThe organic phase isolated
  4. washis washed twice with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated down
  7. customthe remaining residue is purified by chromatography over silica gel (9:1 ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-416dd162ccea4a349c02f5606a4844b5
Source dataset
uspto-grants-1993_04
Patent number
US05199969

Reaction notes

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