Acetic Anhydride → Methyl 3-(formylamino)-2-thiophenecarboxylate

HRID 1181273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181273
[C:1](OC(=O)C)(=[O:3])C.[CH3:8][O:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[NH2:17])=[O:11]>C(O)=O>[CH3:8][O:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[NH:17][CH:1]=[O:3])=[O:11]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 2777636Methyl 3-(formylamino)-2-thiophenecarboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

Formic acid (40 mL) was added to acetic anhydride (60 mL) while cooling in an ice bath. Solid 3-amino-2-thiophenecarboxylic acid methyl ester (77, 10.3 g, 66 mmol) was added to the cold solution in small portions. The cooling bath was removed and the resulting suspension was stirred at room temperature for 4 hours. The reaction mixture was diluted with water (100 mL) and the solid product collected by vacuum filtration to yield 3-(formylamino)-2-thiophenecarboxylic acid methyl ester (10.3 g, 85% yield) as a white solid.

Aufarbeitung

  1. temperaturewhile cooling in an ice bath
  2. customThe cooling bath was removed
  3. additionThe reaction mixture was diluted with water (100 mL)
  4. filtrationthe solid product collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-ed02863559cd41839cd258b368e6d40f
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285556B2

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