Dimethyl Sulfate → HCID 57500737, compound

HRID 2380786Notes

Reaction equation

HRID 2380786 reaction equation
[OH:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[C:4]([C:11]([O:13][CH3:14])=[O:12])[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[C:18](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:18][O:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[C:4]([C:11]([O:13][CH3:14])=[O:12])[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 57500736HCID 57500736, compound

Product 1

HCID 57500737HCID 57500737, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 4-hydroxy-5-(methoxycarbonyl)-3-nitrothiophene-2-carboxylate (650 mg, 2.5 mmol) in acetone (20 mL) was added potassium carbonate (0.68 g, 5 mmol) at it Dimethyl sulfate (0.36 mL, 3.73 mmol) was added to the above reaction mixture slowly with stirring and a catalytic amount of KI was added. The mixture was refluxed for 4 h and the cooled reaction mixture was filtered and the solids were washed with acetone. Acetone was removed under reduced pressure and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10) as eluents to give the product as a pale yellow color solid (0.3 g, 45%), mp 80-82° C. 1H NMR (400 MHz, CDCl3): δ 4.08 (3H, s), 3.94 (3H, s), 3.92 (3H, s).

Workup

  1. additionwas added to the above reaction mixture slowly
  2. additiona catalytic amount of KI was added
  3. temperatureThe mixture was refluxed for 4 h
  4. customthe cooled reaction mixture
  5. filtrationwas filtered
  6. washthe solids were washed with acetone
  7. customAcetone was removed under reduced pressure
  8. customthe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-5ecb0d5d3bbb4051b9f3fa1e5ad586d6
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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