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Cyclobutanone → tert-Butyl cyclobutylidenecarbazate

HRID 12918
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12918
[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.[C:6]([O:10][C:11]([NH:13][NH2:14])=[O:12])([CH3:9])([CH3:8])[CH3:7]>CCCCCC>[C:6]([O:10][C:11]([NH:13][N:14]=[C:1]1[CH2:4][CH2:3][CH2:2]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14496CyclobutanoneHCID 70091tert-Butyl carbazate

Produkt 1

HCID 45092398tert-Butyl cyclobutylidenecarbazateAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

The reaction mixture of cyclobutanone (15 g, 214 mmol) and hydrazinecarboxylic acid tert-butyl ester (28.3 g, 214 mmol) in hexane (225 mL) was heated to reflux for 2 hours. After cooling down, a precipitate formed and the solid was filtered under vacuum. Isopropanol (10 mL) and hexane (100 mL) were added to the solid and the mixture was put on the rotary evaporator under vacuum until a slurry was generated. After filtration, the solid was washed with hexane twice and dried in vacuo to afford N′-cyclobutylidene-hydrazinecarboxylic acid tert-butyl ester (32 g, 81%) as white solid which was used without further purification.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling down
  4. customa precipitate formed
  5. filtrationthe solid was filtered under vacuum
  6. additionIsopropanol (10 mL) and hexane (100 mL) were added to the solid
  7. customthe mixture was put on the rotary evaporator under vacuum until a slurry
  8. filtrationAfter filtration
  9. washthe solid was washed with hexane twice
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8077ea87bc5b4e968bb24e3cbfde846c
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728029B2

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