4-Fluorophenyl isothiocyanate → HCID 86662261, Verbindung

HRID 1627397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1627397
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:17])([CH3:16])[C:12]([NH:14][NH2:15])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:17])([CH3:16])[C:12]([NH:14][NH:15][C:26](=[S:27])[NH:25][C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

4

Edukt 2

HCID 152414-Fluorophenyl isothiocyanateHCID 66740370HCID 66740370, Verbindung

Produkt 1

HCID 86662261HCID 86662261, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(3,4-dimethoxyphenyl)-2-methylpropanehydrazide (1.04 g, 4.37 mmol) and 4-fluorophenyl isothiocyanate (1.34 g, 8.73 mmol) in EtOH (30 mL) was heated at reflux 2 h. The reaction mixture was cooled and filtered. The filtrate was concentrated in vacuo and the residue was triturated with Et2O. The solids were collected by filtration and dried in vacuo to give 2-(2-(3,4-dimethoxyphenyl)-2-methylpropanoyl)-N-(4-fluorophenyl)hydrazinecarbothioamide (1.23 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ 9.70 (br s, 1H), 9.65 (br s, 1H), 7.38 (b, 1H), 7.17 (t, 3H), 6.94-6.82 (m, 4H), 3.73 (s, 3H), 3.71 (s, 3H), 1.52 (s, 6H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux 2 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was triturated with Et2O
  7. filtrationThe solids were collected by filtration
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8e998b9c7b8a4ec2a93796aca0363281
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785488B2

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