Diethyl Ether → 1,4-Dichloroisoquinoline-7-sulfonyl chloride

HRID 1067243

Reaktionsgleichung

Reaktionsgleichung von HRID 1067243
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([S:17]([Cl:20])(=[O:19])=[O:18])=[CH:14][CH:15]=2)[C:10](=O)[NH:9][CH:8]=1.CCOCC>CC#N>[Cl:20][S:17]([C:13]1[CH:12]=[C:11]2[C:16]([C:7]([Cl:6])=[CH:8][N:9]=[C:10]2[Cl:3])=[CH:15][CH:14]=1)(=[O:19])=[O:18]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 24813Phosphorus oxychlorideHCID 166583514-Chloro-1-oxo-1,2-dihydroisoquinoline-7-sulfonyl chloride

Produkt 1

HCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chlorideAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Phosphorus oxychloride (POCl3) (9.65 mL, 103.5 mmol) was added to a stirred suspension of 4-chloro-7-chlorosulphonyl-1-(2H)-isoquinolone (22.1 g, 79.6 mmol) in MeCN (500 mL) at room temperature and the mixture was then heated at reflux for 15 h. On cooling, the MeCN solution was decanted from the insoluble sludge and evaporated in vacuo. The residue was extracted with hot EtOAc and evaporated to leave a solid which was stirred with Et2O (1.2 L) at room temperature overnight. The ethereal solution was decanted from the insoluble material and evaporated in vacuo to give 7-chlorosulphonyl-1,4-dichloroisoquinoline (20 g, 67 mmol) as a pale yellow solid.

Aufarbeitung

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 15 h
  3. temperatureOn cooling
  4. customthe MeCN solution was decanted from the insoluble sludge
  5. customevaporated in vacuo
  6. extractionThe residue was extracted with hot EtOAc
  7. customevaporated
  8. customto leave a solid which
  9. customThe ethereal solution was decanted from the insoluble material
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c24f4ee4e02941e2b8badf179b698531
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248738B1

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