Triethylamine → N-cyclohexyl-N'-hexadecylsulfamide

HRID 640032

Reaktionsgleichung

Reaktionsgleichung von HRID 640032
[CH:1]1([NH:7][S:8](Cl)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:12]([NH2:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH:1]1([NH:7][S:8]([NH:28][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8926HexadecylamineHCID 10340Sodium CarbonateHCID 12914615Cyclohexylsulfamyl chloride

Produkt 1

HCID 68579003N-cyclohexyl-N'-hexadecylsulfamideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 13.6 g of the cyclohexylsulfamoyl chloride (69 mmol) in 100 mL of dichloromethane is added under argon atmosphere to a solution of 1-hexadecylamine (19.9 g, 82 mmol) and triethylamine (47.5 mL, 340 mmol) in 300 mL of dichloromethane. The reaction mixture is stirred 5 hours at 0° C., neutralized with an aqueous Na2CO3 solution and concentrated under reduced pressure. The residue is taken up in dichloromethane (800 mL). The organic components are successively washed with diluted hydrochloric aqueous solution, NaHCO3 aqueous solution and brine, dried (Na2SO4), and concentrated under reduced pressure. The residue is suspended in ether, filtered through Büchner, and the precipitate is washed two times with 100 ml of ether to yield a white powder of N-cyclohexyl-N′-hexadecylsulfamide (21.8 g, 79%).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. washThe organic components are successively washed
  3. additionwith diluted hydrochloric aqueous solution, NaHCO3 aqueous solution and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. filtrationfiltered through Büchner
  7. washthe precipitate is washed two times with 100 ml of ether

Quellen und Nachweise

ORD-Eintrag
ord-2ce0015573b343abbf3d7d36d0f5e3e1
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691929B2

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