Water → 3-bromo-4-(bromomethyl)-N-[(trimethysilyl)methyl]benzamide

HRID 1873468Notes

Reaction equation

HRID 1873468 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][Br:12])[C:5](O)=[O:6].[CH3:13][Si:14]([CH3:18])([CH3:17])[CH2:15][NH2:16].Cl.CN(C)CCCN=C=NCC.O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][Br:12])[C:5]([NH:16][CH2:15][Si:14]([CH3:18])([CH3:17])[CH3:13])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 874881-(Trimethylsilyl)methylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 116163143-bromo-4-(bromomethyl)benzoic Acid

Product 1

HCID 580920793-bromo-4-(bromomethyl)-N-[(trimethysilyl)methyl]benzamideYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-bromo-4-(bromomethyl)benzoic acid (5 g), 1-(trimethylsilyl)methylamine (1.76 g), N,N-dimethylaminopyridine (0.1 g) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (4.3 g) were dissolved in dichloromethane (30 ml), and stirred for 5 hours at room temperature. Water was added to the reaction mixture, and then organic layer was separated and dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 3-bromo-4-(bromomethyl)-N-[(trimethysilyl)methyl]benzamide (4 g).

Workup

  1. customorganic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtering the reaction mixture
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-758cc12b0c254ba58d19fd20e19c37e7
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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