HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Water → [4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrile
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Dimethylformamide | HCID 6228 | — |
| Edukt | Sodium Cyanide | HCID 8929 | — |
| Edukt | 2-[4-(Bromomethyl)-3-chlorophenyl]-1,3-benzoxazole | HCID 21990985 | — |
| Lösungsmittel | Sodium chloride; water | HCID 57417360 | — |
| Produkt | [4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrile | HCID 10286072 | — |
Reaktionsschritte
A slurry of NaCN (435 mg, 8.9 mmol), 2-[4-(bromomethyl)-3-chlorophenyl]-1,3-benzoxazole (940 mg, 2.9 mmol), DMF (30 mL) and H2O (30 mL) was stirred at rt for 12 h. The reaction mixture was poured into brine (250 mL) and filtered. The resultant colorless solid was purified by flash chromatography on silica gel (EtOAc:hexanes 1:9) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.32 (s, 1H), 8.19 (dd, 1H), 7.77–7.80 (m, 1H), 7.70 (d, 1H), 7.59–7.61 (m, 1H), 7.38–7.41 (m, 2H), 3.92 (s, 2H). MS (ESI) 269 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07087601B2 |
| Quelldatensatz | uspto-grants-2006_08 |
| ORD ID | ord-6548a23538894aa79436e59d15d367bc |
| Quellennotiz | uspto-grants-2006_08 |