Cyclopropylamine → 2-(Trimethylsilyl)ethyl 3-(cyclopropylsulfamoyl)benzoate

HRID 1025425

Reaktionsgleichung

Reaktionsgleichung von HRID 1025425
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])(=[O:4])=[O:3].[CH:20]1([NH2:23])[CH2:22][CH2:21]1>N1C=CC=CC=1>[CH:20]1([NH:23][S:2]([C:5]2[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=2)[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])(=[O:4])=[O:3])[CH2:22][CH2:21]1

Komponenten

4

Edukt 2

HCID 69828CyclopropylamineHCID 866763342-(Trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate

Produkt 1

HCID 712384462-(Trimethylsilyl)ethyl 3-(cyclopropylsulfamoyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 2.00 g of 2-(trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate, 1.2 mL of cyclopropylamine, and 20 mL of pyridine was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and to the residue was added an aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with 1.0 M hydrochloric acid and saturated brine in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2.12 g of 2-(trimethylsilyl)ethyl 3-(cyclopropylsulfamoyl)benzoate as a pale yellow oily substance. EI: 341

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added an aqueous citric acid solution
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with 1.0 M hydrochloric acid and saturated brine in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ae01795146524e578c6a8793948035df
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729068B2

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