Benzoyl isocyanate → N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide

HRID 44338

Reaktionsgleichung

Reaktionsgleichung von HRID 44338
[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]=[O: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)=[O:21])#[N:8]

Komponenten

4

Edukt 2

HCID 78210Benzoyl isocyanateHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

Produkt 1

HCID 57456902N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamideAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-4,5-dimethylthiophene-3-carbonitrile (example 4b) (25 g, 164.5 mmol) in 1.4-dioxane (600 mL) was added benzoyl isocyanate (24.2 g, 164.5 mmol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The precipitate was collected by filtration, washed with 1.4-dioxane (20 mL×3), and dried under vacuum at 40° C. for 3 hours to give N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide (44.35 g, 90%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ2.10 (s, 3H), 2.24 (s, 3H), 7.52-7.56 (m, 2H), 7.64-7.69 (m, 1H), 8.01-8.03 (m, 2H), 11.57 (brs, 1H), 12.05 (brs, 1H). MS 300 (MH+).

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with 1.4-dioxane (20 mL×3)
  3. customdried under vacuum at 40° C. for 3 hours

Quellen und Nachweise

ORD-Eintrag
ord-8d622ce8eff24443b3fa8ee750c7b985
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541421B2

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