Dimethylformamide → 6-(5-Isoquinolylsulfanyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-one

HRID 619739

Reaktionsgleichung

Reaktionsgleichung von HRID 619739
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([SH:11])[C:5]=2[CH:4]=[CH:3][N:2]=1.F[C:13]1[C:14]([N+:23]([O-:25])=[O:24])=[CH:15][C:16]2OC(=O)N[C:17]=2[CH:22]=1.[C:26](=[O:29])([O-])[O-:27].[K+].[K+].C[N:33](C=O)C>>[CH:1]1[C:10]2[C:5](=[C:6]([S:11][C:13]3[C:14]([N+:23]([O-:25])=[O:24])=[CH:15][C:16]4[NH:33][C:26](=[O:29])[O:27][C:17]=4[CH:22]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 110519635-IsoquinolinethiolHCID 112178355-Fluoro-6-nitro-2,3-dihydro-1,3-benzoxazol-2-one

Produkt 1

HCID 218469496-(5-Isoquinolylsulfanyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-oneAusbeute 38 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

5-Isoquinolinethiol 500 mg (3.1 mmol) was dissolved in DMF 20 ml, 5-fluoro-6-nitro-benzooxazolinone 670 mg (3.1 mmol) and potassium carbonate 1.29 g (9.3 mmol) were added, and the mixture was heated with stirring overnight at 130° C. The reaction mixture was concentrated under reduced pressure, acetone 20 ml was added to the residue, and insoluble materials were filtered. Chloroform 50 ml was added to the organic layer, the resulting precipitates were collected to give 6-(5-isoquinolylsulfanyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-one 400 mg (38.0%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure, acetone 20 ml
  3. additionwas added to the residue, and insoluble materials
  4. filtrationwere filtered
  5. additionChloroform 50 ml was added to the organic layer
  6. customthe resulting precipitates
  7. customwere collected

Quellen und Nachweise

ORD-Eintrag
ord-d846d0a1c7c44e54b7b9fb5c6f5cbeca
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05959107

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