Tert-Butylamine → ethyl-2-(N-tert-butylsulfamoyl)acetate

HRID 553464

Reaktionsgleichung

Reaktionsgleichung von HRID 553464
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH2:6]([O:8][C:9]([CH2:11][S:12](Cl)(=[O:14])=[O:13])=[O:10])[CH3:7]>C1COCC1>[CH2:6]([O:8][C:9](=[O:10])[CH2:11][S:12](=[O:14])(=[O:13])[NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:7]

Komponenten

4

Edukt 2

HCID 6385Tert-ButylamineHCID 12225100Ethyl (chlorosulfonyl)acetate

Produkt 1

HCID 19833529ethyl-2-(N-tert-butylsulfamoyl)acetateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

tert-Butylamine (7.9 mL, 75 mmol.) was dissolved in 50 mL of THF. The solution was cooled to −20° C. and (ethoxycarbonyl)methanesulfonyl chloride dissolved in 10 mL of THF was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 24 h. The mixture was filtered, and the filtrate concentrated in vacuo. The residue was purified by column chromatography (PE/EtOAc; 2:1) to afford ethyl-2-(N-tert-butylsulfamoyl)acetate (4.1 g, 43%).

Aufarbeitung

  1. additionwas added slowly
  2. temperatureto warm to room temperature
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified by column chromatography (PE/EtOAc; 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-794c0450771447b48a4f95417416d507
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048862B2

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