Benzoyl isothiocyanate → N-benzoyl-N'-(3-cyano-4,5-dimethyl-2-thienyl)thiourea

HRID 471466

Reaktionsgleichung

Reaktionsgleichung von HRID 471466
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[C:11]([N:19]=[C:20]=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCOCC1>[C:7]([C:6]1[C:5]([CH3:9])=[C:4]([CH3:10])[S:3][C:2]=1[NH:1][C:20]([NH:19][C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[S:21])#[N:8]

Komponenten

4

Edukt 2

HCID 68284Benzoyl isothiocyanateHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

Produkt 1

HCID 899430N-benzoyl-N'-(3-cyano-4,5-dimethyl-2-thienyl)thiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-4,5-dimethylthiophene-3-carbonitrile (1.52 g, 10.0 mmol) in 1,4-dioxane (20 mL) was added benzoylisothiocyanate (1.63 g, 10.0 mmol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The precipitation was collected by filtration, washed with EtOAc/Hexanes (1:4), and dried under vacuum overnight to give N-(3-Cyano-4,5-dimethylthiophen-2-ylcarbamothioyl)benzamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.23 (s, 3H), 2.31 (s, 3H), 7.58-7.54 (m, 2H), 7.68-7.66 (m, 1H), 7.94 (d, J=7.2 Hz, 2H), 9.13 (bs, 1H). MS 316 (MH+).

Aufarbeitung

  1. customThe precipitation
  2. filtrationwas collected by filtration
  3. washwashed with EtOAc/Hexanes (1:4)
  4. customdried under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-4f8f9a9edec64f1abf3b4b0c887b8a32
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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