Maleic Anhydride → 1-Methoxycarbonyl-3-[2-(3-carboxyacrylamido)phenyl]thiourea

HRID 1415654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1415654
[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])=[S:7])=[O:4].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH:18]=[CH:17]1>C(O)C>[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:22])[CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[S:7])=[O:4]

Komponenten

4

Edukt 2

HCID 7923Maleic AnhydrideHCID 3032830Thiophamine

Produkt 1

HCID 536421621-Methoxycarbonyl-3-[2-(3-carboxyacrylamido)phenyl]thioureaAusbeute 28,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-methoxycarbonyl-3-(2-aminophenyl)thiourea (10.9 g., 0.048 mole), maleic anhydride (4.7 g; 0.048 mole) and ethanol (200 ml) was boiled under reflux with stirring for one hour. The clear solution was allowed to cool and the crystals which deposited were filtered off. These were recrystallised once from ethanol and once from a mixture of acetone and petroleum spirit (b.p. 60°-80° C.) to give 1-methoxycarbonyl-3-[2-(3-carboxyacrylamido)phenyl]thiourea (4.4 g) m.p. 170°-173° C. (with decomposition).

Aufarbeitung

  1. temperatureunder reflux
  2. temperatureto cool
  3. filtrationthe crystals which deposited were filtered off
  4. customThese were recrystallised once from ethanol and once from a mixture of acetone and petroleum spirit (b.p. 60°-80° C.)

Quellen und Nachweise

ORD-Eintrag
ord-4d05abead64c4abab4a08021772a2f2d
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04005217

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