Ethylene Glycol → Benzylaniline

HRID 2179301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179301
[CH2:1]([NH:8][C:9](=O)[C:10](F)(F)F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].I[C:24]1[CH:29]=CC=[CH:26][CH:25]=1.C(O)CO.CCCCCCCCCCCC.N>C(OCC)(=O)C.[Cu]I.C(O)(C)C>[C:9]1([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=[CH:26][CH:25]=[CH:24][CH:29]=1

Komponenten

10

Edukt 6

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 8182DodecaneHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 230121N-Benzyl-2,2,2-trifluoroethanimidic acid

Produkt 1

HCID 66028BenzylanilineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), N-benzyl-trifluoroacetamide (244 mg, 1.20 mmol), K3PO4 (640 mg, 3.01 mmol), evacuated, backfilled with Ar. Iodobenzene (112 μL, 1.00 mmol), ethylene glycol (0.11 mL, 2.0 mmol), and isopropanol (1.5 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 80° C. for 24 h. The resulting white suspension was allowed to reach room temperature. Dodecane (internal GC standard, 230 μL), ethyl acetate (2 mL), and 30% aq ammonia (2 mL) were added. A 0.1 mL sample of the top layer was diluted with ethyl acetate (1 mL) and analyzed by GC to provide a 76% yield of N-phenylbenzylamine.

Aufarbeitung

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature

Quellen und Nachweise

ORD-Eintrag
ord-41477a406db0480f9d5e730713c1f0ff
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067955B2

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