Sodium hydride → HCID 89690341, compound

HRID 2202867Notes

Reaction equation

HRID 2202867 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].[H-].[Na+].[Cl-].[Cl-].[Ca+2].[CH3:18][O:19][CH2:20][C:21](Cl)=[O:22]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([N:7]([CH3:8])[C:21](=[O:22])[CH2:20][O:19][CH3:18])[CH:9]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 96623Methoxyacetyl chlorideHCID 5284359Calcium Chloride2×HCID 106095305-bromo-N-methyl-2-nitroaniline

Product 1

HCID 89690341HCID 89690341, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-N-methyl-2-nitroaniline (500 mg) in THF (10 ml) was added NaH (40% oil dispersion, 104 mg) at 0° C. The mixture was stirred at 0° C. under a dry atmosphere (CaCl2 tube) for 30 min. After being stirred, methoxyacetyl chloride (0.237 ml) was added to the reaction mixture. The mixture was stirred at 60° C. under a dry atmosphere (CaCl2 tube) for 3 h and then at room temperature overnight. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc). The resulting solid was washed with Et2O to give the title compound (478 mg) as a pale yellow solid.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe mixture was quenched with water
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)
  10. washThe resulting solid was washed with Et2O

Sources & evidence

ORD record
ord-49f999c070614f399b0b5cdc4f330c25
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…