Bromoacetic Acid → 2-Bromo-N-[3-(trimethoxysilyl)propyl]acetamide

HRID 1067182Notes

Reaction equation

HRID 1067182 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=O.[CH3:6][O:7][Si:8]([O:15][CH3:16])([O:13][CH3:14])[CH2:9][CH2:10][CH2:11][NH2:12]>Cl.CN(C)CCCN=C=NCC.C(Cl)Cl>[CH3:6][O:7][Si:8]([O:13][CH3:14])([O:15][CH3:16])[CH2:9][CH2:10][CH2:11][NH:12][C:3](=[O:5])[CH2:2][Br:1]

Participants

5

Reactant 2

HCID 6227Bromoacetic AcidHCID 83756Aminopropyltrimethoxysilane

Product 1

HCID 224811332-Bromo-N-[3-(trimethoxysilyl)propyl]acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideSolvent

Procedure

Binder DNA oligonucleotide-derivatized porous silicon films were employed to test the selectivity and limits of detection of a contemplated sensor. For attachment of DNA, a trimethoxy-3-bromoacetamido-propylsilane linker was synthesized by reaction of bromoacetic acid with trimethoxy-(3-aminopropyl)silane in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide-hydrochloride in methylene chloride as solvent. The linker product was purified by column chromatography on silica gel. The oxidized porous silicon samples were then contacted with a toluene solution of the linker for 2 hours. The resulting linker-bound substrate was thoroughly rinsed with pure toluene and methylene chloride, and dried for about 18 hours under reduced pressure.

Workup

  1. customThe linker product was purified by column chromatography on silica gel
  2. washThe resulting linker-bound substrate was thoroughly rinsed with pure toluene and methylene chloride
  3. customdried for about 18 hours under reduced pressure

Sources & evidence

ORD record
ord-2de7dc0003074e959375b22cd35d64da
Source dataset
uspto-grants-2001_06
Patent number
US06248539B1

Reaction notes

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