1,3-Dichloroacetone → 4-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazole

HRID 322273

Reaktionsgleichung

Reaktionsgleichung von HRID 322273
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH2:8])=[O:7].[Cl:9][CH2:10][C:11]([CH2:13]Cl)=O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:9][CH2:10][C:11]1[N:8]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[O:7][CH:13]=1

Komponenten

5

Edukt 3

HCID 107931,3-DichloroacetoneHCID 11430Potassium CarbonateHCID 220632-Thiophenecarboxamide

Produkt 1

HCID 25295314-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazoleAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-thiophenecarboxamide (5.09 g) and 1,3-dichloroacetone (457 g) was stirred at 120° C. for 2 hours. The reaction mixture was poured into water, nautralized with potassium carbonate, and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with diethyl ether-hexane (1:9, v/v), 4-chloromethyl-2-(2-thienyl)oxazole (4.09 g, 57%) was obtained. Recrystallization from isopropylether gave colorless needles, mp 59-59° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. washFrom the fraction eluted with diethyl ether-hexane (1:9, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-c0f2cf7c7df84db1a690d728e4081640
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211215B1

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