Chloroacetonitrile → HCID 14279665, Verbindung

HRID 1381817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381817
[F:1][C:2]1[C:12]([N:13]2[C:21](=[O:22])[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]2=[O:23])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:31][C:32]#[N:33]>C(#N)C>[F:1][C:2]1[C:12]([N:13]2[C:21](=[O:22])[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]2=[O:23])=[CH:11][C:5]2[N:6]([CH2:31][C:32]#[N:33])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 137721852-(7-Fluoro-3-oxo-4H-1,4-benzoxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione

Produkt 1

HCID 14279665HCID 14279665, VerbindungAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A suspension of 2-[7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (2 g) and potassium carbonate (1.05 g) in acetonitrile (30 ml) is refluxed for 30 minutes. The resulting solution is cooled to a temperature of 5° C. To the solution is added dropwise chloroacetonitrile (0.72 g), and thereafter the solution is refluxed for 3 hours. The solvent is distilled off, and the residue is admixed with water and subjected to an extraction operation with the aid of dichloromethane. The dichloromethane layer is separated off, washed with water, and dried over sodium sulfate. The solution is concentrated to precipitate a crystalline product, which is then recrystallized in a solvent consisting of acetonitrile and water. As an end product, 2-[7-fluoro-4-cyanomethyl-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.84 g) is obtained. mp. 216°-220° C.

Aufarbeitung

  1. temperatureis refluxed for 30 minutes
  2. temperaturethe solution is refluxed for 3 hours
  3. distillationThe solvent is distilled off
  4. customThe dichloromethane layer is separated off
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationThe solution is concentrated
  8. customto precipitate a crystalline product, which
  9. customis then recrystallized in a solvent

Quellen und Nachweise

ORD-Eintrag
ord-6932387b295e4072bd3e5db202965271
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04804394

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