1,2-Dichloroethane → HCID 16244366, Verbindung

HRID 2043327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2043327
ClC1C=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(O[BH-](O[C:19](=O)[CH3:20])OC(=O)C)(=O)C.[Na+].[C:23](O)(=O)[CH3:24].C(=O)(O)[O-].[Na+].Cl[CH2:33][CH2:34][Cl:35]>ClCCl>[Cl:35][C:34]1[CH:23]=[C:24]([NH:5][CH2:4][CH:6]2[CH2:7][CH2:8]2)[CH:19]=[CH:20][CH:33]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 79323-ChloroanilineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 16244366HCID 16244366, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-chloroaniline (1.27 g, 10 mmol) in 1,2-dichloroethane (20 ml) were added molecular sieves (4 g, size 0.4 nM) and cyclopropanecarboxyaldehyde (0.7 g, 10 mmol). After stirring the mixture for 5 min at room temperature sodium triacetoxyborohydride (3.18 g, 15 mmol) and acetic acid (0.6 g, 10 mmol) were added. The reaction mixture was stirred at room temperature overnight. For workup dichloromethane (100 ml) and 1 M sodium bicarbonate solution (40 ml) were added and the mixture was shaken. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (heptane/ethyl acetate=9:1) to yield a colourless liquid (1.09 g, 60%); MS (EI): 181.1 (M+.).

Aufarbeitung

  1. additionwere added
  2. stirringthe mixture was shaken
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-49cd08961d8f433d91f6473ffda554f9
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586617B2

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