Thionyl Chloride → HCID 14279665, Verbindung

HRID 2291771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2291771
[C:1]([CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([N:16]3[C:24](=[O:25])[C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[C:17]3=[O:26])[C:13]([F:15])=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:27])(=O)[NH2:2].S(Cl)(Cl)=O>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([N:16]3[C:17](=[O:26])[C:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=4[C:24]3=[O:25])[C:13]([F:15])=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:27])#[N:2]

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 14347810HCID 14347810, Verbindung

Produkt 1

HCID 14279665HCID 14279665, VerbindungAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

N,N-dimethylformamide (3 drops) was added to a mixture consisting of 2-[4-carbamoylmethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.2 g), toluene (30 ml) and thionyl chloride (0.2 g), and then the mixture was refluxed under heating for 3 hours. After the solvent was concentrated, toluene (50 ml) was added and fully mixed therewith, and then toluene was distilled off. The resulting solid was recrystalled from ethanol to give the desired 2-[4-cyanomethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.15 g). mp. 225°-229° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. concentrationAfter the solvent was concentrated
  4. additiontoluene (50 ml) was added
  5. additionfully mixed
  6. distillationtoluene was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-6facb16927f34d51be7e96de3080bb5f
Quelldatensatz
uspto-grants-1989_01
Patentnummer
US04798620

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