Water → 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide

HRID 241517

Reaktionsgleichung

Reaktionsgleichung von HRID 241517
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[Cl:11].[NH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15].O>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[O:7])=[CH:4][C:3]=1[Cl:11]

Komponenten

5

Edukt 3

HCID 962WaterHCID 874881-(Trimethylsilyl)methylamineHCID 125943024-Bromo-3-chlorobenzoic acid

Produkt 1

HCID 668366994-bromo-3-chloro-N-trimethylsilanylmethyl-benzamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a suspension of 4-bromo-3-chlorobenzoic acid (25.00 g, 106.2 mmol) in CH2Cl2 (320 mL) was added N,N-dimethyl aminopyridine (1.95 g), followed by N-ethyl-N-dimethylamine propylcarbodiimide hydrochloride (22.39 g) in small portions. After 30 min at room temperature, aminomethyl trimethylsilane (11.2 g, 7.87 mL, 108 mmol) was added while maintaining the temperature at 20° C. After stirring over night, water was added and the organic layer was separated. The aqueous layer was extracted twice with CH2Cl2 and the combined organic phases were dried and evaporated in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (34.00 g, 100%).

Aufarbeitung

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice with CH2Cl2
  3. customthe combined organic phases were dried
  4. customevaporated in vacuum
  5. customThe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e86fb4dcd46743ff948c85722bfc7573
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653000B2

Verknüpfte Notizen

Wird geladen…