Thionyl Chloride → 4-(Chloromethyl)-2-(propan-2-yl)-1,3-oxazole

HRID 53928

Reaktionsgleichung

Reaktionsgleichung von HRID 53928
[Cl:1][CH2:2][C:3]1(O)[CH2:7][O:6][C:5]([CH:8]([CH3:10])[CH3:9])=[N:4]1.O=S(Cl)Cl>ClCCCl>[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[O:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 107498144-Chloromethyl-4-hydroxy-2-isopropyoxazoline

Produkt 1

HCID 27632914-(Chloromethyl)-2-(propan-2-yl)-1,3-oxazoleAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 4-chloromethyl-4-hydroxy-2-isopropyloxazoline (4.88 g, 0.0275 mol) in 1,2-dichloroethane (20 mL) was added to a solution of SOCl2 (2.40 mL, 0.0329 mol)in 1,2-dichloroethane (80 mL) at 0° C. under argon, and the solution was heated to 70° C. After 15 min at 70° C., the reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. Drying the residue on high vacuum gave the desired compound as a brown semi-solid (4.20 g, 0.0263 mol, 96%): 1H NMR (CDCl3) δ 1.36 (d, J=7.5 Hz, 6H), 3.03-3.18 (m, 1H), 4.50 (s, 2H), 7.56 (s, 1H). Mass spectrum: (M+H)+ =160, 162.

Aufarbeitung

  1. temperaturethe reaction was cooled to room temperature
  2. customthe solvent removed by rotary evaporation in vacuo
  3. customDrying the residue on high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6c53a1862e104e9882f1032a9ff2f155
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05621109

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