m-Chloroperbenzoic acid → bis(4-Fluorophenyl)methyl(5-methylsulfinyl-1H-1,2,4-triazol-1-ylmethyl)silane

HRID 568776Notes

Reaction equation

HRID 568776 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([CH3:17])[CH2:9][N:10]2[C:14]([S:15][CH3:16])=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)([CH3:17])[CH2:9][N:10]2[C:14]([S:15]([CH3:16])=[O:33])=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14154947bis(4-Fluorophenyl)methyl(5-methylthio-1H-1,2,4-triazol-1-ylmethyl)silane

Product 1

HCID 14154948bis(4-Fluorophenyl)methyl(5-methylsulfinyl-1H-1,2,4-triazol-1-ylmethyl)silaneYield 111.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.8 g (0.005 mol) of bis(4-fluorophenyl)methyl(5-methylthio-1H-1,2,4-triazol-1-ylmethyl)silane in 15 mL of methylene chloride cooled to 0° C. was added 1.1 g (0.005 mol) of m-chloroperbenzoic acid (80%). The reaction temperature rose to 10°. The reaction mixture was stirred at 25° for 3 hours, then diluted with methylene chloride, washed with 7% aqueous NaHCO3 and brine, dried over Na2SO4 and evaporated to give 2.1 g of the title compound as an oil, pure except for traces of solvent and starting material: nD 1.5717; ir (neat) 3020, 1590, 1500, 1232, 1164, 1110, 1070, 825 cm-1 ; nmr (CDCl3) δ 0.7 (3H, s), 2.8 (3H, s), 4.6 (2H, ABq), 7.1 (4H, m), 7.5 (4H, m), 7.9 (1H, s).

Workup

  1. customrose to 10°
  2. washwashed with 7% aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-353ecf28c7ae4132b9dc3cb866cbf08b
Source dataset
uspto-grants-1988_03
Patent number
US04729986

Reaction notes

Loading…