(Chloromethyl)bis(4-fluorophenyl)methylsilane → 1-[Bis(4-fluorophenyl)methylsilylmethyl]-1,2,4-Triazole

HRID 1534784Notes

Reaction equation

HRID 1534784 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[Na].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([SiH2:22][CH2:23]Cl)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1>CN(C)C=O.O>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([SiH2:22][CH2:23][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 5463758(Chloromethyl)bis(4-fluorophenyl)methylsilaneHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 1018265211-[Bis(4-fluorophenyl)methylsilylmethyl]-1,2,4-Triazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In this preparation 1.0 g of sodium 1,2,4-triazole is added to a solution of 3.1 g of bis(4-fluorophenyl)methylsilylmethyl chloride in 15 mL of dimethylformamide. The mixture is heated at about 80°-90° C. for two hours and then cooled to room temperature. The mixture is then diluted with 60 ml of water and extracted three times with 50 ml portions of ethyl ether. The extracts are combined, washed twice with 80 ml of water, then with 80 ml of aqueous saturated sodium chloride solution and dried over magnesium sulfate. The ethyl ether solvent is evaporated off affording an oil which is then purified by chromatography over silica gel solution with ethyl acetate, hexane, and mixture thereof.

Workup

  1. temperatureThe mixture is heated at about 80°-90° C. for two hours
  2. extractionextracted three times with 50 ml portions of ethyl ether
  3. washwashed twice with 80 ml of water
  4. dry with materialwith 80 ml of aqueous saturated sodium chloride solution and dried over magnesium sulfate
  5. customThe ethyl ether solvent is evaporated off
  6. customaffording an oil which
  7. customis then purified by chromatography over silica gel solution with ethyl acetate, hexane, and mixture

Sources & evidence

ORD record
ord-ec99d17b88a547fb874f6df38344d57d
Source dataset
uspto-grants-1992_02
Patent number
US05091377

Reaction notes

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