Hydrochloric Acid → HCID 178514157, Verbindung

HRID 1452769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452769
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH:3]=1.C([N:22]=[C:23]=[S:24])(=O)C1C=CC=CC=1.[OH-].[Na+].Cl>C1COCC1>[Cl:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:3]=[C:2]([NH:1][C:23]([NH2:22])=[S:24])[NH:6][N:5]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68284Benzoyl isothiocyanateHCID 178507276HCID 178507276, Verbindung

Produkt 1

HCID 178514157HCID 178514157, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-3-(2-chlorophenyl)pyrazole (3.8 g, 19.6 mmol) in THF (150 mL) was added dropwise benzoyl isothiocyanate (2.9 mL, 21.56 mmol). The reaction mixture was stirred at room temperature for 4 hours, then 4 N aqueous solution of NaOH (8 mL) was added, and the reaction mixture was further stirred at room temperature for 17 hours. The reaction mixture was neutralized to pH 7 with 1 N aqueous HCl, and extracted with EtOAc (3×). The combined organic layers were directly purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent to provide 3.47 g (72 % yield) of [5-(2-chloro-phenyl)-2H-pyrazol-3-yl]-thiourea as a tan solid.

Aufarbeitung

  1. stirringthe reaction mixture was further stirred at room temperature for 17 hours
  2. extractionextracted with EtOAc (3×)
  3. customThe combined organic layers were directly purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent

Quellen und Nachweise

ORD-Eintrag
ord-2e01dcf821464f1a95a1d08c5abab07f
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473783B2

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