(Chloromethyl)(4-chlorophenyl)dimethylsilane → (4-Chlorophenyl)dimethyl(1H-imidazol-1-ylmethyl)silane

HRID 2413307

Reaction equation

HRID 2413307 reaction equation
Cl[CH2:2][Si:3]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].[Na].[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>CN(C)C=O.O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([Si:3]([CH3:5])([CH3:4])[CH2:2][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 2733089(Chloromethyl)(4-chlorophenyl)dimethylsilaneHCID 57373095Imidazole sodium

Product 1

HCID 20430362(4-Chlorophenyl)dimethyl(1H-imidazol-1-ylmethyl)silaneYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.2 g (0.010 mol) of chloromethyl(4-chlorophenyl)dimethylsilane and 1.1 g (0.012 mol) of imidazole sodium salt in 5 ml of dimethylformamide was stirred at 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 2.0 g (81%) of the title compound as a yellow liquid: nD20 1.5472; ir (neat) 1560, 1495, 1480, 1375, 1250, 1105, 1080, 905, 830, 810, 740 cm-1 ; nmr (CDCl3) 0.3 (6H, s), 3.6 (2H, s), 6.6 (1H, broad s), 6.9 (1H, broad s), 7.1 (1H, broad s), 7.3 (4H, s).

Workup

  1. temperaturecooled
  2. extractionextracted with ether
  3. washThe ether solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-7f7f78be48114def9b364ce1bab25c3c
Source dataset
uspto-grants-1985_01
Patent number
US04496551

Linked notes

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