Thionyl Chloride → 2-(2,4-Dichloro-6-methoxyphenyl)-4,4-dimethyl-2-oxazoline

HRID 354584

Reaktionsgleichung

Reaktionsgleichung von HRID 354584
O[CH2:2][C:3]([NH:6][C:7](=[O:18])[C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([Cl:16])=[CH:10][C:9]=1[Cl:17])([CH3:5])[CH3:4].S(Cl)(Cl)=O>CCOCC>[Cl:17][C:9]1[CH:10]=[C:11]([Cl:16])[CH:12]=[C:13]([O:14][CH3:15])[C:8]=1[C:7]1[O:18][CH2:2][C:3]([CH3:4])([CH3:5])[N:6]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 128028822,4-dichloro-N-(1-hydroxy-2-methylpropan-2-yl)-6-methoxybenzamide

Produkt 1

HCID 128028832-(2,4-Dichloro-6-methoxyphenyl)-4,4-dimethyl-2-oxazolineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

N-(2-Hydroxy-1,1-dimethylethyl)-2,4-dichloro-6-methoxybenzamide (5.5 g, 18.8 mmol) was treated dropwise with thionyl chloride (5.5 ml) and stirred magnetically at 20° C. for 30 min. Dry ether (100 ml) was added, the mixture was stirred for an additional one hour and the oxazoline hydrochloride precipitate was collected by filtration. The salt was neutralized with 20% sodium hydroxide to afford an alkaline mixture which was extracted with ether. The ethereal extract was dried (MgSO4) and concentrated to give an oil (3.6 g, 70%), which crystallized on standing, mp 47°-50° C.

Aufarbeitung

  1. stirringthe mixture was stirred for an additional one hour
  2. filtrationthe oxazoline hydrochloride precipitate was collected by filtration
  3. customto afford an alkaline mixture which
  4. extractionwas extracted with ether
  5. extractionThe ethereal extract
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1ddf7d7c733b4071b781c2021aeec1fe
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04375475

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