Dimethyl acetylenedicarboxylate → HCID 12437416, Verbindung

HRID 1448678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448678
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3]([O:5][CH3:6])=[O:4].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2OC(=O)[S:22][N:21]=2)=[CH:16][CH:15]=1)([O-:13])=[O:12]>C(OCC)(=O)C>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:1]([C:7]([O:9][CH3:10])=[O:8])[S:22][N:21]=2)=[CH:18][CH:19]=1)([O-:13])=[O:12]

Komponenten

4

Edukt 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 12437399(4-Nitrophenyl)-1,3,4-oxathiazol-2-one

Produkt 1

HCID 12437416HCID 12437416, VerbindungAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dimethyl acetylenedicarboxylate (85.26 g, 0.6 mol) and 5-(p-nitrophenyl)-1,3,4-oxathiazol-2-one (33.63 g, 0.15 mol) were heated as given above for 15 hours. Crystallization of the brown solid from methanol (2X) gave little improvement in purity. The brown solid was decolorized in ethyl acetate solution and recrystallized (3X) to give 12.2 g (0.0378 mol, 25.2%) of dark gold solid, m.p. 142°-143°.

Aufarbeitung

  1. customas given above for 15 hours
  2. customCrystallization of the brown solid from methanol (2X)
  3. customgave little improvement in purity
  4. customrecrystallized (3X)

Quellen und Nachweise

ORD-Eintrag
ord-a0897120cf9542af9a82bebdd8e5cc24
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04187099

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