Iodoethane → 2-Chloro-N-(2-ethoxyethyl)-N-ethyl-6-(trimethylsilyl)benzamide

HRID 1060104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060104
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:13][CH2:14][CH2:15][NH:16][C:17](=[O:29])[C:18]1[C:23]([Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:28])[CH3:12].[CH2:30](I)[CH3:31]>C1COCC1>[Cl:28][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([Si:24]([CH3:27])([CH3:26])[CH3:25])[C:18]=1[C:17]([N:16]([CH2:15][CH2:14][O:13][CH2:11][CH3:12])[CH2:30][CH3:31])=[O:29]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18630026N-(2-ethoxyethyl)-2-chloro-6-(trimethylsilyl)benzamide

Produkt 1

HCID 186302162-Chloro-N-(2-ethoxyethyl)-N-ethyl-6-(trimethylsilyl)benzamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A 1M THF solution of sodium bis(trimethylsilyl)amide (7.7 mL, 7.7 mmol) was added dropwise over 5 min to a solution of N-(2-ethoxyethyl)-2-chloro-6-(trimethylsilyl)benzamide (2.1 g, 7 mmol) in THF (30 mL). The resulting mixture was stirred for 1 h at RT, then a solution of ethyl iodide (1.31 g, 8.4 mmol) in THF (15 mL) was added with a mild exotherm. The resulting reaction mixture was stirred overnight, then was partitioned between ethyl acetate and dilute aq citric acid. The ethyl acetate phase was washed with sat aq NaHCO3 followed with brine, then was dried (MgSO4) and concentrated to afford 1.9 g of the title compound as an amber oil, an 83% yield.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringwas stirred overnight
  3. customwas partitioned between ethyl acetate and dilute aq citric acid
  4. washThe ethyl acetate phase was washed with sat aq NaHCO3
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-22a38bc1ecb946828c21a9e50ea111bd
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521603B2

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