Water → 4-bromo-3-methyl-N-(trimethylsilylmethyl)benzamide

HRID 241524

Reaktionsgleichung

Reaktionsgleichung von HRID 241524
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[CH3:11].CN(C)CCCN=C=NCC.[NH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26].O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:7])=[CH:4][C:3]=1[CH3:11]

Komponenten

7

Edukt 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 821314-Bromo-3-methylbenzoic acidHCID 874881-(Trimethylsilyl)methylamine

Produkt 1

HCID 668364694-bromo-3-methyl-N-(trimethylsilylmethyl)benzamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 4-bromo-3-methylbenzoic acid (25 g) and 4-(dimethylamino)pyridine (“DMAP”, 2.1 g) in CH2Cl2 (320 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (“EDC”, 22.4 g) portionwise. Then, (aminomethyl)trimethylsilane (8.6 mL) was added, while cooling to keep the internal temperature below 20° C. The reaction was stirred at room temperature overnight. Water was added under vigorous stirring, and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic phase dried (Na2SO4), and filtered over silica gel using CH2Cl2 and methyl tert-butyl ether (MTBE) to afford the title compound (32.8 g, 94%).

Aufarbeitung

  1. temperaturewhile cooling
  2. customthe internal temperature below 20° C
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted twice with CH2Cl2
  5. dry with materialthe combined organic phase dried (Na2SO4)
  6. filtrationfiltered over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-84bff735b8e84773b38a246cec69f299
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653000B2

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