Acetone → 4-[(2-Cyanopropan-2-yl)amino]-2-fluoro-N-methylbenzamide

HRID 515798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515798
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.[Si]([C:17]#[N:18])(C)(C)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[CH3:31][C:32]([CH3:34])=O>C(Cl)Cl>[C:17]([C:32]([NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1)([CH3:34])[CH3:31])#[N:18]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 65367Trimethylsilyl triflateHCID 82115Trimethylsilyl cyanideHCID 441395214-Amino-2-fluoro-N-methylbenzamide

Produkt 1

HCID 592965474-[(2-Cyanopropan-2-yl)amino]-2-fluoro-N-methylbenzamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-amino-2-fluoro-N-methylbenzamide (2 g, 11.9 mmol), TMSCN (2.2 mL, 17.9 mmol), TMSOTf (0.1 mL, 0.6 mmol), and acetone (10 mL, 140 mmol) in DCM (20 mL) was stirred at room temperature overnight. The white solid was filtered, washed with a small amount of DCM, and dried to afford 1.12 g of 4-((2-cyanopropan-2-yl)amino)-2-fluoro-N-methylbenzamide as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.79 (t, 1H), 7.56 (t, 1H), 6.88 (s, 1H), 6.67 (dd, 1H), 6.54 (dd, 1H), 2.75 (d, 3H), 1.67 (s, 6H).

Aufarbeitung

  1. filtrationThe white solid was filtered
  2. washwashed with a small amount of DCM
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d9cc09fa78ed43669f81b39b6b08c6bf
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108944B2

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