Dodecane → N-(3,5-dimethylphenyl)-N-methylformamide

HRID 1243125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243125
CN1[CH2:6][CH2:5][N:4]([C:7]2N(C)C=CN=2)[C:3]1=[O:13].[O-]P([O-])([O-])=O.[K+].[K+].[K+].I[C:23]1[CH:24]=[C:25]([CH3:30])[CH:26]=C(C)[CH:28]=1.CNC=O.CCCCCCCCCCCC>C(OCC)(=O)C.[Cu]I.C1(C)C=CC=CC=1>[CH3:30][C:25]1[CH:26]=[C:5]([N:4]([CH3:7])[CH:3]=[O:13])[CH:6]=[C:23]([CH3:28])[CH:24]=1

Komponenten

9

Edukt 5

HCID 8182DodecaneHCID 31254N-MethylformamideHCID 62657Potassium Phosphate, TribasicHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 219406413,1'-dimethyl-4,5-dihydro-3H,1'H-[1,2']biimidazolyl-2-one

Produkt 1

HCID 9855564N-(3,5-dimethylphenyl)-N-methylformamideAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 3,1′-dimethyl-4,5-dihydro-3H,1′H-[1,2′]biimidazolyl-2-one (18 mg, 0.10 mmol, 10 mol %), K3PO4 (430 mg, 2.03 mmol), evacuated, backfilled with Ar. 5-Iodo-m-xylene (145 μL, 1.00 mmol), N-methylformamide (72 μL, 1.23 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 24 h. The suspension was allowed to reach room temperature. Dodecane (internal GC standard, 230 μL) and ethyl acetate (2 mL) were added. A 0.1 mL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide 54% yield of N-(3,5-dimethylphenyl)-N-methylformamide.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-043513e747564d02821506d95a1ca7e4
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115784B2

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