Water → (E)-1-(3-chlorophenyl)-N-(trimethylsilylmethyl)methanimine

HRID 2065401Notes

Reaction equation

HRID 2065401 reaction equation
[NH2:1][CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4].[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O.O>ClCCl>[Cl:7][C:8]1[CH:9]=[C:10](/[CH:11]=[N:1]/[CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 114773-ChlorobenzaldehydeHCID 874881-(Trimethylsilyl)methylamine

Product 1

HCID 58399006(E)-1-(3-chlorophenyl)-N-(trimethylsilylmethyl)methanimineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (aminomethyl)trimethylsilane (Fluka) (1.6 g, 16 mmol) in dichloromethane (100 mL) was added 3-chloro-benzaldehyde (Aldrich) (1.9 g, 14 mmol). The reaction mixture was stirred at room temperature for 3 h. Water was added. The organic layer was separated, washed with brine, dried over MgSO4, and concentrated to give [1-(3-chloro-phenyl)-meth-(E)-ylidene]-trimethylsilanylmethyl-amine as a colorless oil (3 g, 95%).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a8cb789802244bd588278303ab4cd1d0
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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