Thionyl Chloride → 4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

HRID 1178249

Reaktionsgleichung

Reaktionsgleichung von HRID 1178249
[O:1]=[C:2]1[C:6]2[N:7]=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[NH:4][N:3]1[C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1.S(Cl)([Cl:26])=O>>[O:1]=[C:2]1[C:6]2[N:7]=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[NH:4][N:3]1[C:15]1[CH:23]=[CH:22][C:18]([C:19]([Cl:26])=[O:20])=[CH:17][CH:16]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 589749144-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoic acid

Produkt 1

HCID 589748734-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

Versuchsvorschrift

Thionyl chloride (90 ml) was added to 4-(3-oxo-1,3-dihydro-2H-pyrazolo-[4,3-c]cinnolin-2-yl)benzoic acid (2.36 g, 7.70 mmol). The mixture was heated to reflux for 2 h under nitrogen atmosphere. A dark red solution was obtained, cooled to room temperature and excess thionyl chloride was removed under vacuum. Toluene (30 ml) was added to the residues and the mixture was stirred at room temperature under nitrogen atmosphere until precipitation was complete. The solids were collected by filtration and washed with toluene (2×30 ml). The title compound was isolated as a red solid (2.20 g, 6.77 mmol, 88%) LCMS: m/z 321 [M+H]+ (methyl ester resulting from sample make-up in methanol).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h under nitrogen atmosphere
  3. customA dark red solution was obtained
  4. customexcess thionyl chloride was removed under vacuum
  5. additionToluene (30 ml) was added to the residues
  6. filtrationThe solids were collected by filtration
  7. washwashed with toluene (2×30 ml)

Quellen und Nachweise

ORD-Eintrag
ord-52f4bac1e2494535a9f03b9949f717b7
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276505B2

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