Water → 4-(bromomethyl)-N-[(trimethylsilyl)methyl]naphthalene-1-carboxamide

HRID 1873475Notes

Reaction equation

HRID 1873475 reaction equation
[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=O)=[CH:5][CH:4]=1.[CH3:16][Si:17]([CH3:21])([CH3:20])[CH2:18][NH2:19].Cl.CN(C)CCCN=C=NCC.O>ClCCl>[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([NH:19][CH2:18][Si:17]([CH3:21])([CH3:20])[CH3:16])=[O:15])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 874881-(Trimethylsilyl)methylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109783504-(bromomethyl)naphthalene-1-carboxylic Acid

Product 1

HCID 580920724-(bromomethyl)-N-[(trimethylsilyl)methyl]naphthalene-1-carboxamideYield 32.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(bromomethyl)naphthalen-1-carboxylic acid (7 g), 1-(trimethylsilyl)methylamine (2.7 g), N,N-dimethylaminopyridine (0.1 g) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (6.6 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 layers, were 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 4-(bromomethyl)-N-[(trimethylsilyl)methyl]naphthalene-1-carboxamide (3 g).

Workup

  1. customorganic layers, were 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-bbba0753b84f493ba611971039387096
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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