N-Ethyl-p-toluenesulfonamide → N-Ethyl-4-methyl-N-phenylbenzenesulfonamide

HRID 984652

Reaktionsgleichung

Reaktionsgleichung von HRID 984652
[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].CN[C@@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]1NC.IC1C=CC=CC=1>[Cu]I.C1(C)C=CC=CC=1>[CH2:1]([N:3]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 6637N-Ethyl-p-toluenesulfonamideHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Produkt 1

HCID 74568N-Ethyl-4-methyl-N-phenylbenzenesulfonamideAusbeute 868,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A 15 mL resealable Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol %), N-ethyl-p-toluenesulfonamide (240 mg, 1.20 mmol), K2CO3 (280 mg, 2.03 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (16 μL, 0.102 mmol, 10 mol %), iodobenzene (112 μL, 1.00 mmol) and toluene (1 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 23 h. The resulting pale brown suspension was allowed to reach room temperature and then filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×15 cm, hexane-ethyl acetate 4:1, 15 mL fractions). Fractions 10-17 provided 244 mg (89% yield) of the desired product.

Aufarbeitung

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel (2×15 cm, hexane-ethyl acetate 4:1, 15 mL fractions)

Quellen und Nachweise

ORD-Eintrag
ord-48d94cd9dfff4c0eb6e099101de45914
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867298B2

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