Benzoyl isocyanate → N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide

HRID 471626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471626
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH3:11])[C:3]=1[C:4]#[N:5].[C:12]([N:20]=[C:21]=[O:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCOCC1>[C:4]([C:3]1[C:6]([NH:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][C:21]([NH:20][C:12](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:22])#[N:5]

Komponenten

4

Edukt 2

HCID 78210Benzoyl isocyanateHCID 127157172-Amino-6-(methylamino)benzonitrile

Produkt 1

HCID 67401506N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-6-(methylamino)benzonitrile (example 156b) (0.14 g, 0.97 mmol) in 1,4-dioxane (3 mL) was added benzoyl isocyanate (0.17 g, 1.17 mmol). The reaction mixture was stirred at room temperature under nitrogen overnight. The obtained precipitate was filtered and dried under vacuum to give N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide (57 mg, 20%). 1H NMR (400 MHz, DMSO-d6) δ 2.75 (d, J=4.4 Hz, 3H), 6.26 (d, J=4.8 Hz, NH), 6.43 (d, J=9.6 Hz, 1H), 7.40-7.43 (m, 2H), 7.51-7.55 (m, 2H), 7.63-7.65 (m, 1H), 8.01 (d, J=8.4 Hz, 2H), 11.23 (s, NH), 11.30 (s, NH). MS 295 (MH+).

Aufarbeitung

  1. filtrationThe obtained precipitate was filtered
  2. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0550d2542d9746a79cce10b578bc590c
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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