Dimethyl Sulfate → N-methyl-N-(2-nitrophenyl)acetamide

HRID 987206Notes

Reaction equation

HRID 987206 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])([O-:5])=[O:4].[C:13](OC(=O)C)(=[O:15])[CH3:14].S(OC)(O[CH3:24])(=O)=O>O1CCCC1.O>[CH3:24][N:8]([C:13](=[O:15])[CH3:14])[C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[N+:3]([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 69462-NitroanilineHCID 7918Acetic AnhydrideHCID 24758Sodium hydride

Product 1

HCID 3521078N-methyl-N-(2-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.58 g of sodium hydride (60% content) was suspended in 19.8 g of tetrahydrofuran and cooled with ice. To the obtained suspension, 19.8 g of a tetrahydrofuran solution containing 2.50 g of 2-nitroaniline was added dropwise over 1 hr, stirred for 10 minutes, allowed to stand at room temperature and stirred for 30 minutes. To the obtained mixture, 2.01 g of acetic acid anhydride was added over 1 hr at room temperature and stirred for 2 hours. To the reaction mixture, 2.49 g of dimethyl sulfate were added at room temperature and stirred for 1 hr. The reaction mixture was added to water and the separated organic layer was washed with saline then the organic layer was analyzed by high performance liquid chromatography to find the yield of the desired product was 78%.

Workup

  1. temperaturecooled with ice
  2. additionwas added dropwise over 1 hr
  3. customto stand at room temperature
  4. stirringstirred for 30 minutes
  5. stirringstirred for 2 hours
  6. stirringstirred for 1 hr
  7. washthe separated organic layer was washed with saline

Sources & evidence

ORD record
ord-5e61f275c00b461c884c92bc901f8295
Source dataset
uspto-grants-2003_10
Patent number
US06630598B2

Reaction notes

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