Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 80217Erstellt: 25. Oktober 2026

Methanol → 3-(Benzothiazol-6-ylamino)-butyric acid

https://huagongshe.com/reaction/80217

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktMethanolHCID 887—
EduktPotassium CarbonateHCID 11430—
EduktEthyl 3-aminobutyrateHCID 98103—
Edukt6-Iodo-1,3-benzothiazoleHCID 22609002—
KatalysatorCopper iodideHCID 83717—
LösungsmittelChloroformHCID 6212—
LösungsmittelDimethylformamideHCID 6228—
Produkt3-(Benzothiazol-6-ylamino)-butyric acidHCID 5963619122,22%

Reaktionsbedingungen

Temperatur110 °C

Reaktionsschritte

3-Amino-butyric acid ethyl ester (2 g, 15.27 mmol), 6-iodo-benzothiazole (3.98 g. 15.27 mmol) and potassium carbonate (5.27 g, 38.18 mmol) were dissolved in DMF (50 mL) and the reaction mixture was purged with argon for 10 minutes. This was followed by the addition of copper iodide (290 mg, 1.527 mmol) and the resulting mixture was heated to 110° C. overnight. The reaction was monitored by TLC (10% MeOH in CHCl3) which showed the presence of starting material. The reaction mixture was heated to 120° C. for a further 24 hours. The reaction mixture was concentrated and adjusted the pH to 5 using acetic acid. The reaction mixture was partitioned between water and ethylacetate. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 800 mg of the product (22.22% yield).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUSRE045173E1
Quelldatensatzuspto-grants-2014_09
ORD IDord-1bff1dbf7917497a89502f5a5837242e
Quellennotizuspto-grants-2014_09