Dimethyl Sulfoxide → 2-Anilinothiazole-4-carbaldehyde

HRID 2107261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2107261
CS(C)=O.[NH:5]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][OH:18])[N:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>O>[NH:5]([C:12]1[S:13][CH:14]=[C:15]([CH:17]=[O:18])[N:16]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 15053553HCID 15053553, Verbindung

Produkt 1

HCID 150535702-Anilinothiazole-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A dimethyl sulfoxide solution (120 ml) of 20 g of sulfur trioxide pyridine complex was added dropwise to a mixture comprising 8.3 g of 2-anilinothiazol-4-ylmethanol, 16.5 ml of triethylamine and 120 ml of dimethyl sulfoxide. The resulting mixture was stirred at room temperature for 10 minutes and then poured into water. followed by extraction with ethyl acetate. The extract was washed successively with aqueous acetic acid, aqueous sodium chloride solution and aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The residue afforded by evaporation of the solvent under reduced pressure was recrystallized from a mixture of benzene and acetone. The resulting product was a brown powder having the following physical properties.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed successively with aqueous acetic acid, aqueous sodium chloride solution and aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue afforded by evaporation of the solvent under reduced pressure
  5. customwas recrystallized from a mixture of benzene and acetone

Quellen und Nachweise

ORD-Eintrag
ord-cec89db97521440fba29f14be0d6d555
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04933355

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