Thionyl Chloride → 3-(Chloromethyl)-1-isopropylazetidine hydrochloride

HRID 273077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 273077
[ClH:1].[CH:2]([N:5]1[CH2:8][CH:7]([CH2:9]O)[CH2:6]1)([CH3:4])[CH3:3].S(Cl)([Cl:13])=O>ClCCl>[ClH:13].[Cl:1][CH2:9][CH:7]1[CH2:8][N:5]([CH:2]([CH3:4])[CH3:3])[CH2:6]1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 68575734(1-Isopropylazetidin-3-yl)methanol hydrochloride

Produkt 1

HCID 685790653-(Chloromethyl)-1-isopropylazetidine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(1-isopropylazetidin-3-yl)methanol hydrochloride (2.6 g, 15.7 mmol) was dissolved in dichloromethane (50 ml) and cooled to 0° C. Thionyl chloride (1.4 ml, 19.2 mmol) was added dropwise over 5 min. The reaction mixture was then stirred whilst warming to ambient temperature. Stirred at ambient temperature for 48 hours. The reaction mixture was concentrated in vacuo and azeotroped with toluene (40 ml) to give the title compound as a beige hygroscopic powder (2.8 g, 99%). LRMS ESI+ m/z 148/150 [M+H]+ (CI isotopes).

Aufarbeitung

  1. temperaturewhilst warming to ambient temperature
  2. stirringStirred at ambient temperature for 48 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customazeotroped with toluene (40 ml)

Quellen und Nachweise

ORD-Eintrag
ord-18d6e1fc4fb24465aa3f87e8ba92bbe4
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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