Dimethylformamide → HCID 121386223, compound

HRID 2202854Notes

Reaction equation

HRID 2202854 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[NH:7][CH3:8].[CH3:13][C:14]([CH3:20])([CH3:19])[CH2:15][C:16](Cl)=[O:17].CN(C=O)C.[H-].[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([N:7]([CH3:8])[C:16](=[O:17])[CH2:15][C:14]([CH3:20])([CH3:19])[CH3:13])[CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 815143,3-Dimethylbutanoyl chlorideHCID 106095305-bromo-N-methyl-2-nitroaniline

Product 1

HCID 121386223HCID 121386223, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 5-bromo-N-methyl-2-nitroaniline (300 mg), 3,3-dimethylbutanoyl chloride (0.450 ml) and DMF (5 ml) was added NaH (40% oil dispersion, 57.1 mg), and the mixture was heated at 70° C. overnight. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (214 mg) as a solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-3c931fb1e8e44af382c081e75b012c6b
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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