Triethylamine → HCID 66920960, Verbindung

HRID 1363866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363866
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].Br[CH:9]([OH:11])[CH3:10].[CH3:12][Si:13]([CH:16]([NH2:21])[Si:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:14].C(N(CC)CC)C>ClCCl>[CH3:12][Si:13]([CH:16]([NH:21][S:2]([N:5]1[CH2:10][CH2:9][O:11][C:6]1=[O:7])(=[O:4])=[O:3])[Si:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:14]

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 70918Chlorosulfonyl isocyanateHCID 10997564Bis(trimethylsilyl)methylamineHCID 14202443Ethanol, 1-bromo-

Produkt 1

HCID 66920960HCID 66920960, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel4×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 2.18 ml of chlorosulfonyl isocyanate in 10 ml of dichloromethane is added dropwise, at 0° C., a solution of 1.77 ml of bromoethanol in 10 ml of dichloromethane. The reaction medium is stirred for 10 minutes at 0° C. and then added dropwise to a solution of 4.38 grams of bis(trimethylsilyl)methylamine and 3.51 ml of triethylamine in 40 ml of dichloromethane at 0° C. After warming to 20° C. and stirring for 4 hours, the reaction mixture is cooled to 0° C. and 10.5 ml of triethylamine are then added dropwise. The reaction mixture is then stirred overnight at room temperature. It is then diluted with dichloromethane and washed 3 times with dilute hydrochloric acid. The organic phase is then washed once with saturated aqueous NaCl solution and then dried over sodium sulfate and concentrated under reduced pressure to give a white solid, 2-oxooxazolidine-3-sulfonic acid [bis(trimethylsilanyl)methyl]amide (65% yield).

Aufarbeitung

  1. temperatureAfter warming to 20° C.
  2. stirringstirring for 4 hours
  3. temperaturethe reaction mixture is cooled to 0° C.
  4. stirringThe reaction mixture is then stirred overnight at room temperature
  5. washwashed 3 times with dilute hydrochloric acid
  6. washThe organic phase is then washed once with saturated aqueous NaCl solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3bef8fd6a3484fb88a7830e35b175cb2
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07887824B2

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