Dimethyl Sulfate → HCID 9856789, compound

HRID 1167242Notes

Reaction equation

HRID 1167242 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[C:4]([CH3:17])[CH:3]=1.[C:18](=O)([O-])[O-].[Cs+].[Cs+].COS(OC)(=O)=O>CN(C=O)C.C(OCC)(=O)C.[OH-].[Na+]>[CH3:18][O:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:12])=[O:13])=[C:4]([CH3:17])[CH:3]=1

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 22996562HCID 22996562, compound

Product 1

HCID 9856789HCID 9856789, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-hydroxy-2-methyl-5-nitro(N,N-dimethyl)benzenesulfonamide (100 mg, 0.39 mmol) in dry DMF (1 mL) was added cesium carbonate (125 mg, 0.39 mmol) and dimethylsulfate (50 mg, 0.39 mmol). The resulting reaction mixture was heated to 60° C. and stirred for 3 h. After cooling to room temperature, the reaction was diluted with ethyl acetate and 1 N NaOH. The layers were separated, and the organics were washed once with 1 N NaOH. The organics were then dried and concentrated to provide 4-methoxy-2-methyl-5-nitro(N,N-dimethyl) benzenesulfonamide (90 mg, 85%) as a yellow solid, mp 130-132° C. Mass spectrum ES+: 275.0 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. customThe layers were separated
  4. washthe organics were washed once with 1 N NaOH
  5. customThe organics were then dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-604f97e27f2f4eacaec1511ba78ad77b
Source dataset
uspto-grants-2003_09
Patent number
US06617357B2

Reaction notes

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