Dimethyl Sulfate → 4-Methoxy-N-methyl-3-nitrobenzeneacetamide

HRID 975927Notes

Reaction equation

HRID 975927 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH3:12])=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.S([O-])(OC)(=O)=O>CN(C=O)C.O>[CH3:16][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH3:12])=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 4694097Methyl sulfate(1-)HCID 134095334-hydroxy-N-methyl-3-nitrobenzeneacetamide

Product 1

HCID 134095344-Methoxy-N-methyl-3-nitrobenzeneacetamideYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.2 g (19.8 mmol) of 4-hydroxy-N-methyl-3 -nitrobenzeneacetamide in 50 mL of DMF containing 5.5 g of anhydrous potassium carbonate was added 5.6 mL of dimethyl sulfate. The mixture was heated at 60°-70° C. for 45 min, treated with an additional 3.0 mL of methyl sulfate, and heated for another 30 min. The mixture was cooled, poured into 200 mL water, and extracted with dichloromethane. The extracts were washed with water, dried and evaporated to give a solid which was recrystallized from ethanol-water to afford 3.7 g of a yellowish solid (82%). 1H NMR (300 MHz, CDCl3) δ 7.71 (s, 1H), 7.47 (d, 1H, J =9.0 Hz), 7.25 (d, 1H, J =8.4 Hz), 5.71 (brs, 1H), 3.90 (s, 3H) 3.47 (s, 2H), 2.75 (d, 3H, J=4.8 Hz).

Workup

  1. temperatureThe mixture was heated at 60°-70° C. for 45 min
  2. temperatureheated for another 30 min
  3. temperatureThe mixture was cooled
  4. extractionextracted with dichloromethane
  5. washThe extracts were washed with water
  6. customdried
  7. customevaporated
  8. customto give a solid which
  9. customwas recrystallized from ethanol-water

Sources & evidence

ORD record
ord-9296010060b6485aba8463c6a3b5e3eb
Source dataset
uspto-grants-1997_03
Patent number
US05610174

Reaction notes

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