HCID 13392351, compound → (1,1'-biphenyl-4-yl)dimethyl(1H-1,2,4-triazol-1-ylmethyl)silane

HRID 1980517Notes

Reaction equation

HRID 1980517 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH2:10]Cl)([CH3:9])[CH3:8])=[CH:3][CH:2]=1.[Na].[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1>CN(C)C=O.O>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH3:9])([CH3:8])[CH2:10][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 13392351HCID 13392351, compoundHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 13474675(1,1'-biphenyl-4-yl)dimethyl(1H-1,2,4-triazol-1-ylmethyl)silaneYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.6 g (0.010 mol) of (1,1'-biphenyl-4-yl)chloromethyldimethylsilane and 1.1 g (0.012 mol) of 1,2,4-triazole sodium salt in 5 ml of dimethylformamide was warmed to 80°-90° for 2 hours, cooled, diluted with water, and extracted with ether. The ether solution was washed with water and brine, dried over magnesium sulfate, and evaporated to leave 2.3 g of colorless solid, m.p. 79°-86°. Recrystallization from a mixture of 25 ml of hexanes and 2 ml of ethyl acetate gave 1.1 g (38%) of the title compound: m.p. 92°-93°; ir (Nujol®) 1255, 1130, 1000, 825, 760, 695 cm-1 ; nmr (CDCl3) 0.4 (6H, s), 3.9 (2H, s), 7.2-7.7 (9H, m), 7.8 (1H, s), 7.9 (1H, s); analysis for C17H19N3Si (mw 293.43):

Workup

  1. temperaturewas warmed to 80°-90° for 2 hours
  2. temperaturecooled
  3. extractionextracted with ether
  4. washThe ether solution was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d575d9d7177145f39b448f38f74df4b5
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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