Dimethylformamide → HCID 72360033, Verbindung

HRID 1881642

Reaktionsgleichung

Reaktionsgleichung von HRID 1881642
CN(C)C=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([C:20](=O)[CH3:21])[C:15]=2[OH:23])[CH:10]=[CH:11][C:12]=1[Cl:13].[NH:24]([C:26]([NH:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[C:31]([N+:39]([O-:41])=[O:40])[CH:30]=1)=[S:27])[NH2:25]>Cl.O>[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([C:20](=[N:25][NH:24][C:26]([NH:28][C:29]3[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[C:31]([N+:39]([O-:41])=[O:40])[CH:30]=3)=[S:27])[CH3:21])[C:15]=2[OH:23])[CH:10]=[CH:11][C:12]=1[Cl:13]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 60206780HCID 60206780, VerbindungHCID 86014590Methyl 4-hydrazinocarbonothioylamino-2-nitrobenzoate

Produkt 1

HCID 72360033HCID 72360033, VerbindungAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Dimethylformamide (1 ml) and conc. hydrochloric acid (1 drop) were added to 1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone (60 mg, 0.21 mmol) synthesized in Synthetic Example 1 and methyl 4-hydrazinocarbonothioylamino-2-nitrobenzoate (57 mg, 0.21 mmol) synthesized in Reference Synthetic Example 56, and the mixture was stirred at room temperature for 21 hours. Water was added, and the precipitated solid was filtered, purified with a silica gel column chromatography (n-hexane/ethyl acetate=1/1 then chloroform/methanol=95/5). The obtained solid was extracted with ethyl acetate, washed with a saturated ammonium chloride aqueous solution, saturated sodium chloride aqueous solution. The organic layer was concentrated to obtain the desired product as a pale yellow solid (104 mg, yield 92%).

Aufarbeitung

  1. customsynthesized in Reference Synthetic Example 56
  2. filtrationthe precipitated solid was filtered
  3. custompurified with a silica gel column chromatography (n-hexane/ethyl acetate=1/1
  4. extractionThe obtained solid was extracted with ethyl acetate
  5. washwashed with a saturated ammonium chloride aqueous solution, saturated sodium chloride aqueous solution
  6. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-a9109dc970be40a88edd15fe27edfaf7
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318796B2

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