Diethoxy(iodomethyl)phenylsilane → Diethoxy(phenyl)(1H-1,2,4-triazol-1-ylmethyl)silane

HRID 1980532Notes

Reaction equation

HRID 1980532 reaction equation
[CH2:1]([O:3][Si:4]([O:13][CH2:14][CH3:15])([CH2:11]I)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:2].[K].[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[CH2:1]([O:3][Si:4]([O:13][CH2:14][CH3:15])([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:11][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[CH3:2]

Participants

6

Reactant 2

HCID 13474598Diethoxy(iodomethyl)phenylsilaneHCID 534465811,2,4-Triazole potassium

Product 1

HCID 13474668Diethoxy(phenyl)(1H-1,2,4-triazol-1-ylmethyl)silaneYield 79%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4.0 g (0.012 mol) of diethoxy(iodomethyl)phenylsilane, 1.5 g (0.014 mol) of 1,2,4-triazole potassium salt, and 0.5 g (0.14 mmol) of tetrabutylammonium hydrogen sulfate in 10 ml of toluene was stirred and warmed to 100°-110° C. for 5 hours, cooled, diluted with water, and extracted with methylene chloride. The methylene chloride solution was washed with brine, dried over magnesium sulfate, and evaporated to leave 2.6 g (79%) of the title compound as a pale brown oil: nD19 1.5543; ir (neat) 2980, 1590, 1505, 1430, 1270 cm-1 ; nmr (CDCl3) 1.2 (6H, t, J=7), 3.8 (4H, q, J=7), 3.9 (2H, s), 7.2-7.7 (5H, m), 7.8 (s, 1H) and 8.0 (s, 1H).

Workup

  1. temperaturewarmed to 100°-110° C. for 5 hours
  2. temperaturecooled
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride solution was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-6e577615726e48ceb28999cb01ab2ca0
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

Loading…