Thionyl Chloride → 2-[6-(3-[1-Adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-chloro-acetonitrile

HRID 860570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860570
[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH:29](O)[C:30]#[N:31])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O=S(Cl)[Cl:35]>C(Cl)(Cl)Cl.CN(C=O)C>[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH:29]([Cl:35])[C:30]#[N:31])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 865860482-[6-(3-[1-Adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-hydroxy-acetonitrile

Produkt 1

HCID 695836662-[6-(3-[1-Adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-chloro-acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 2-[6-(3-[1-adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-hydroxy-acetonitrile, (0.314 mg, 0.74 mmol) in anhydrous chloroform (10 mL) were added SOCl2 (0.17 mL, 2.23 mmol) and DMF (3 drops). The reaction mixture was heated under reflux for 40 minutes before it was allowed to cool down, washed with water, saturated NaHCO3, brine to give 2-[6-(3-[1-adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-chloro-acetonitrile that was used without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 40 minutes before it
  3. temperatureto cool down
  4. washwashed with water, saturated NaHCO3, brine

Quellen und Nachweise

ORD-Eintrag
ord-8ddf299b0cd947d4b08f2a24c85bf8ea
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153875B2

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