Acetic Anhydride → methyl 3-acetamidothiophene-2-carboxylate

HRID 2358182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2358182
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([O:16][CH3:17])=[O:15]>C1(C)C=CC=CC=1>[C:1]([NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([O:16][CH3:17])=[O:15])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Produkt 1

HCID 729216methyl 3-acetamidothiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

With simultaneous heating in an oil bath, 567 ml of acetic anhydride are added dropwise to a mixture of 942 g of methyl 3-aminothiophene-2-carboxylate and 1000 ml of toluene, and the mixture is then boiled under reflux conditions for 1½ hours and subsequently cooled in an ice bath to about 0° C. The crystals are filtered off and washed twice with a little isopropanol and twice with diisopropyl ether. Methyl 3-acetylaminothiophene-2-carboxylate can be obtained from the filtrate by further concentration and crystallization. M.p. 93-95° C.

Aufarbeitung

  1. temperatureWith simultaneous heating in an oil bath
  2. waitthe mixture is then boiled under reflux conditions for 1½ hours
  3. filtrationThe crystals are filtered off
  4. washwashed twice with a little isopropanol and twice with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2a790b1366ca45c2b46479b8071de76e
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07763643B2

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