2-Thiopheneacetic acid → 2-[5-(Acetamidomethyl)thiophen-2-yl]acetic acid

HRID 224902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 224902
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=[O:8].O[CH2:11][NH:12][C:13](=[O:15])[CH3:14]>FC(F)(F)C(O)=O>[C:13]([NH:12][CH2:11][C:5]1[S:1][C:2]([CH2:6][C:7]([OH:9])=[O:8])=[CH:3][CH:4]=1)(=[O:15])[CH3:14]

Komponenten

4

Edukt 2

HCID 159702-Thiopheneacetic acidHCID 69365Formicin

Produkt 1

HCID 233303672-[5-(Acetamidomethyl)thiophen-2-yl]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

1.42 g of 2-thienylacetic acid are added in portions to a solution, kept at 0°-5° C., of 1.34 g of N-hydroxymethyl acetamide (Einhorn, Ann. Chem., volume 343, page 264 (1905)) in 10 ml of trifluoroacetic acid, whilst stirring. The mixture is stirred for 2 hours at 0°-5° C. and the trifluoroacetic acid is distilled off under reduced pressure. 30 ml of water are added to the residue and the mixture is extracted with twice 50 ml of ethyl acetate. The organic extracts are washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate, concentrated under reduced pressure and filtered through silica gel. The residue is crystallised from ethyl acetate and gives 2-(5-acetylaminomethyl-2-thienyl)-acetic acid, thin layer chromatogram (silica gel): Rf=0.61 (system: butanol/acetic acid/water, 45:45:10); infrared absorption spectrum (mineral oil): characteristic bands at 2.95μ, 5.82μ, 6.23μ and 6.38μ.

Aufarbeitung

  1. stirringThe mixture is stirred for 2 hours at 0°-5° C.
  2. distillationthe trifluoroacetic acid is distilled off under reduced pressure
  3. addition30 ml of water are added to the residue
  4. extractionthe mixture is extracted with twice 50 ml of ethyl acetate
  5. washThe organic extracts are washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. filtrationfiltered through silica gel
  9. customThe residue is crystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7ab72f441ead46f0a1bceb54cbcbabec
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04234578

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