3,5-Dichlorosalicylaldehyde → 3-Trifluoromethoxy-benzoic acid [1-(3,5-dichloro-2-hydroxy-phenyl)-methylidene]-hydrazide

HRID 1255390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255390
[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.[F:12][C:13]([F:26])([F:25])[O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([NH:20][NH2:21])=[O:19]>C(O)C>[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:5]=[N:21][NH:20][C:18](=[O:19])[C:17]2[CH:22]=[CH:23][CH:24]=[C:15]([O:14][C:13]([F:12])([F:26])[F:25])[CH:16]=2)[CH:7]=[C:8]([Cl:10])[CH:9]=1

Komponenten

4

Edukt 2

HCID 666603,5-DichlorosalicylaldehydeHCID 38010993-(Trifluoromethoxy)benzohydrazide

Produkt 1

HCID 1363599553-Trifluoromethoxy-benzoic acid [1-(3,5-dichloro-2-hydroxy-phenyl)-methylidene]-hydrazideAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of 3,5-dichloro-2-hydroxy-benzaldehyde (0.200, 1.05 mmol) and 3-trifluoromethoxy-benzoic acid hydrazide (0.243 g, 1.05 mmol) in ethanol (3.3 mL) was heated to 60° C. for 18 hours. The reaction mixture was cooled to room temperature to precipitate the product. The solid was collected via suction filtration and rinsed with ethanol to furnish 3-trifluoromethoxy-benzoic acid [1-(3,5-dichloro-2-hydroxy-phenyl)-methylidene]-hydrazide as an off-white solid (0.412 g, 99%): mp 180-182° C.; 1H NMR (400 MHz, DMSO) δ 12.63 (s, 1H), 12.39 (s, 1H), 8.60 (s, 1H), 8.01 (d, J=7.6 Hz, 1H), 7.91 (s, 1H), 7.76-7.63 (m, 4H); ESIMS m/z 393 ([M+H]+), 391 ([M−H]−).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto precipitate the product
  3. filtrationThe solid was collected via suction filtration
  4. washrinsed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f3126be4d8164dde9eb6a8eda61a8b66
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461078B2

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