4-Chloro-3-trifluoromethylbenzoic acid hydrazide → HCID 178516245, Verbindung

HRID 661417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661417
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=O)=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].I.CS[C:19](=[NH:28])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[NH:28][C:19]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[N:9][N:8]=2)=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13]

Komponenten

4

Edukt 2

HCID 213117014-Chloro-3-trifluoromethylbenzoic acid hydrazideHCID 178504017HCID 178504017, Verbindung

Produkt 1

HCID 178516245HCID 178516245, VerbindungAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

4-chloro-3-trifluoromethylbenzoic acid hydrazide (2.89 g, 12.1 mmol) and S-methyl N-(4-hydroxyphenyl)isothiourea hydroiodide (3.75 g, 12.1 mmol) were suspended in 40 mL of anhydrous pyridine. The reaction mixture was refluxed for 18 hours, during which time it changed color from yellow into dark-red. Then it was cooled down to ambient temperature and poured with stirring into 250 mL of ice-water. The aqueous solution was decanted and the oily residue was purified by silica gel chromatography using 1:1 mixture of ethyl acetate/hexane. Solvent was removed in vacuo to give the title product as a white solid (1.95 g). Yield 45.5%.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 18 hours, during which time it
  2. additionpoured
  3. customThe aqueous solution was decanted
  4. customthe oily residue was purified by silica gel chromatography
  5. addition1:1 mixture of ethyl acetate/hexane
  6. customSolvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a99d184d11c84f01b3d8631cd54af9c7
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084618B2

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