Ammonium Carbonate → 3-amino-4-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-fluorobenzamide

HRID 1943116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943116
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=2[CH3:27])=[O:8])=[C:5]([F:30])[C:4]=1F)#[N:2].C(=O)([O-])[O-].[NH4+:36].[NH4+]>CS(C)=O>[NH2:36][C:4]1[C:5]([F:30])=[C:6]([CH:28]=[CH:29][C:3]=1[C:1]#[N:2])[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:19])([F:21])[F:20])=[CH:12][C:11]=1[CH3:27])=[O:8]

Komponenten

4

Edukt 2

HCID 517111Ammonium CarbonateHCID 592269444-cyano-2,3-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

Produkt 1

HCID 592269593-amino-4-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-fluorobenzamideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4-cyano-2,3-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (0.693 g, 1.53 mmol) (Example I11) in dimethyl-sulfoxide (2.32 ml) was added ammonium carbonate (69 mg, 1.75 mmol). The reaction mixture was heated to 100° C. for 16 hours. The reaction mixture was allowed to cool to ambient temperature and then partitioned between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3) to give 3-amino-4-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-fluorobenzamide (290 mg, 42% yield). 1H-NMR (400 MHz, CDCl3): 2.35 (6H, s), 4.68 (1H, bs), 7.35-7.41 (4H, m), 7.74 (1H, d) ppm.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-40404f2427184669a9d57054b6f10f39
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389766B2

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