Sodium Cyanide → 4-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-benzamide

HRID 1943120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943120
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[NH:19][C:20](=[O:33])[C:21]1[CH:26]=[C:25]([F:27])[C:24](F)=[C:23]([N+:29]([O-:31])=[O:30])[C:22]=1[F:32].[C-:34]#[N:35].[Na+]>CN(C)C=O>[C:34]([C:24]1[C:25]([F:27])=[CH:26][C:21]([C:20]([NH:19][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([C:8]([F:17])([C:13]([F:15])([F:16])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=2[CH3:18])=[O:33])=[C:22]([F:32])[C:23]=1[N+:29]([O-:31])=[O:30])#[N:35]

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 59226973N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-2,4,5-trifluoro-benzamide

Produkt 1

HCID 592269494-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-benzamideAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-2,4,5-trifluoro-benzamide (6.77 g, 13.75 mmol) (Example I15) in N,N-dimethylformamide (137 ml) at 0° C. was added sodium cyanide (740 mg, 15.13 mmol). The reaction mixture was stirred at 0° C. for one hour and then at ambient temperature for 16 hours. The reaction mixture was concentrated and the residue partitioned between water and dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 8:2) to give 4-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-benzamide (3.2 g, 46.6% yield). 1H-NMR (400 MHz, CDCl3): 2.35 (6H, s), 7.38 (2H, s), 7.83 (1H, d), 8.29 (1H, m) ppm.

Aufarbeitung

  1. customat 0° C.
  2. waitat ambient temperature for 16 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue partitioned between water and dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 8:2)

Quellen und Nachweise

ORD-Eintrag
ord-9c8eb3061c26414ebc0e338972844bcb
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389766B2

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