Dimethyl Sulfate → N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine

HRID 240557

Reaction equation

HRID 240557 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1.S(OC)(O[CH3:28])(=O)=O.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>O.C1(C)C=CC=CC=1>[CH3:28][NH:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:4]=2[CH3:3])=[CH:8][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 11433187Bis(tetrabutylammonium) sulphateHCID 866508954-(2-Methyl-4-nitrophenoxy)-2-nitrobenzenamine

Product 1

HCID 86650896N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamineYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of sodium hydroxide (10.2 g in 10.5 mL water) was added toluene (15 mL), 4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine (2.00 g, 6.92 mmol), dimethyl sulfate (750 μL, 7.88 mmol) and tetrabutylammonium sulfate (0.277 g, 0.816 mmol). After stirring at room temperature, the cooled (0° C.) reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (100 mL). The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was chromatographed (dichloromethane) to provide the product (1.90 g, 91%).

Workup

  1. temperaturethe cooled
  2. custom(0° C.) reaction mixture
  3. extractionextracted with dichloromethane (100 mL)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed (dichloromethane)

Sources & evidence

ORD record
ord-84b6540a481e4829af7f3db48c89bdc2
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Linked notes

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