Water → HCID 59455904, compound

HRID 883055Notes

Reaction equation

HRID 883055 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14](F)=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)=[C:4]([CH3:22])[CH:3]=1.[C-:23]#[N:24].[Na+].O.C(OCC)(=O)C>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([C:23]#[N:24])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)=[C:4]([CH3:22])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium Cyanide2×HCID 59455903HCID 59455903, compound

Product 1

HCID 59455904HCID 59455904, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-bromo-2,6-dimethyl-phenyl)-4-fluoro-3-nitro-benzamide (18.3 g, 49.8 mmol) (Example I1) in N,N-dimethylformamide (115 ml) was added sodium cyanide (2.7 g, 54.8 mmol). The reaction mixture was stirred at ambient temperature for 4 hours, then heated to 60° C. for 16 hours. More sodium cyanide (0.73 g, 14.8 mmol) was added and the reaction mixture was heated to 60° C. for a further 8 hours. The reaction mixture was cooled to ambient temperature before the addition of water (200 ml) and ethyl acetate (100 ml). The organic extract was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1), yielding N-(4-bromo-2,6-dimethyl-phenyl)-4-cyano-3-nitro-benzamide (11.8 g, 63% yield). LC/MS (Method A): 374 (MH+). 1H-NMR (400 MHz, DMSO-d6): 8.91 (s, 1H), 8.53 (d, 1H), 8.4 (d, 1H), 7.4 (s, 2H), 2.2 (s, 6H) ppm.

Workup

  1. temperatureheated to 60° C. for 16 hours
  2. temperaturethe reaction mixture was heated to 60° C. for a further 8 hours
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-7a2586e67e334ec28a3ab7d77f36506c
Source dataset
uspto-grants-2012_08
Patent number
US08236828B2

Reaction notes

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