Carbon Dioxide → Ethyl 3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylate

HRID 1080613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1080613
[C:1]([C:3]([O:5][CH2:6][CH3:7])=[O:4])#[N:2].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2OC(=O)[S:18][N:17]=2)=[CH:12][CH:11]=1.C(=O)=O>CC1C=CC(C)=CC=1>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:2]=[C:1]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:18][N:17]=2)=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 69336Ethyl cyanoformateHCID 8194565-(4-Methoxyphenyl)-1,3,4-oxathiazol-2-one

Produkt 1

HCID 12601460Ethyl 3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7809P-XyleneLösungsmittel

Versuchsvorschrift

Ethyl cyanoformate (16.9 g, 0.171 mol) is added to a stirred solution of 5-(4-methoxyphenyl)-[1,3,4]oxathiazolin-2-one (11.9 g, 0.057 mol) in p-xylene (100 ml). The mixture is heated to 115°-132° C. for 10 hours, during which time carbon dioxide is liberated. The solvent is evaporated in vacuo and the residue is triturated with di-isopropyl ether. The crystalline solid is filtered off, washed with a small amount of diisopropyl ether and dried, to give ethyl 3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylate (11.6 g, 77%) as beige crystals, m.p. 61°-63° C.

Aufarbeitung

  1. customThe solvent is evaporated in vacuo
  2. customthe residue is triturated with di-isopropyl ether
  3. filtrationThe crystalline solid is filtered off
  4. washwashed with a small amount of diisopropyl ether
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-839da68b54ff4eecbda9b2d3fd9e2f68
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05583092

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