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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 2120353Erstellt: 25. Oktober 2026

Oxalyl chloride → (R)-N-(2,3-Dichloro-4-ethylsulphanylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

https://huagongshe.com/reaction/2120353

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktOxalyl chlorideHCID 65578—
Edukt2,6-DiphenylpyridineHCID 72920—
Edukt(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acidHCID 2760712—
Edukt4-Ethylsulphanyl-2,3-dichloroanilineHCID 11183639—
KatalysatorDimethylformamideHCID 6228—
LösungsmittelDichloromethaneHCID 6344—
Produkt(R)-N-(2,3-Dichloro-4-ethylsulphanylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamideHCID 1126844467,7%

Reaktionsschritte

Oxalyl chloride (0.75 ml) was added to a stirred suspension of (R)-(+)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (Method 25) (1.37 g) in DCM (10 ml) containing DMF (1 drop). The mixture was stirred at ambient temperature for 18 hours and was then added to a solution of 4-ethylsulphanyl-2,3-dichloroaniline (Method 7) (1.92 g) and 2,6-diphenylpyridine (2.0 g) in DCM (50 ml). The mixture was stirred for 3 hours at room temperature, volatile material was removed by evaporation and the residue was purified by chromatography eluting with 0-20% EtOAc/isohexane to give the title compound (2.12 g) as a solid. NMR (CDCl3) 1.35 (t, 3H), 1.76 (s, 3H), 2.97 (q, 2H), 3.61 (s, 1H), 7.22 (d, 1H), 8.27 (d, 1H), 8.91 (s, 1H); m/z: 360.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06689909B1
Quelldatensatzuspto-grants-2004_02
ORD IDord-743b6c8217124af89c2f08a782b191e2
Quellennotizuspto-grants-2004_02