HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Oxalyl chloride → (R)-N-(2,3-Dichloro-4-ethylsulphanylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Oxalyl chloride | HCID 65578 | — |
| Edukt | 2,6-Diphenylpyridine | HCID 72920 | — |
| Edukt | (2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid | HCID 2760712 | — |
| Edukt | 4-Ethylsulphanyl-2,3-dichloroaniline | HCID 11183639 | — |
| Katalysator | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | (R)-N-(2,3-Dichloro-4-ethylsulphanylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide | HCID 11268444 | 67,7% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06689909B1 |
| Quelldatensatz | uspto-grants-2004_02 |
| ORD ID | ord-743b6c8217124af89c2f08a782b191e2 |
| Quellennotiz | uspto-grants-2004_02 |