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 1943120Notes

Reaction equation

HRID 1943120 reaction equation
[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]

Participants

4

Reactant 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

Product 1

HCID 592269494-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-benzamideYield 46.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9c8eb3061c26414ebc0e338972844bcb
Source dataset
uspto-grants-2013_03
Patent number
US08389766B2

Reaction notes

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