Phosphorus oxychloride → HCID 16778897, Verbindung

HRID 334517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 334517
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[C:5]([NH:7][NH:8][C:9](=[O:12])[CH2:10][Cl:11])=O.P(Cl)(Cl)(Cl)=O>C(#N)C>[Cl:11][CH2:10][C:9]1[O:12][C:5]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:15]=[C:14]([Cl:16])[CH:13]=2)=[N:7][N:8]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 13365860HCID 13365860, Verbindung

Produkt 1

HCID 16778897HCID 16778897, VerbindungAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 3,5-dichlorobenzohydrazide 5 (0.5 g, 2.4 mmol) and K2CO3 (0.61 g, 4.4 mmol) in acetonitrile (30 mL) was added 2-chloroacetyl chloride (0.41 g, 3.66 mmol) dropwise at ambient temperature. The resulting mixture was stirred at ambient temperature for 16 hours. The solid was collected, washed with H2O and ether, and dried to afford 3,5-dichloro-N′-(2-chloroacetyl)benzohydrazide 6 (0.63 g, 92%) which was used for the next step without further purification. A mixture of 3,5-dichloro-N′-(2-chloroacetyl)benzohydrazide 6 (0.63 g, 2.24 mmol) and phosphorous oxychloride (0.51 g, 3.36 mmol) in acetonitrile (20 mL) was stirred under reflux for 16 hours and concentrated. The residue was subjected to flush column chromatography eluting with 10-25% acetone/hexanes to give compound 7 (0.52 g). Yield: 88%.

Aufarbeitung

  1. customwas used for the next step without further purification
  2. temperatureunder reflux for 16 hours
  3. concentrationconcentrated
  4. customto flush column chromatography
  5. washeluting with 10-25% acetone/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7136fa2362854a15b85529efc6d46b77
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883827B2

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