Dimethyl Sulfate → HCID 53983477, compound

HRID 463865Notes

Reaction equation

HRID 463865 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[OH:7][N:8]=[C:9]([C:15]1[N:16]=[C:17]([CH3:20])[S:18][CH:19]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:1][O:7][N:8]=[C:9]([C:15]1[N:16]=[C:17]([CH3:20])[S:18][CH:19]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 73178131Ethyl 2-hydroxyimino-2-(2-methyl-1,3-thiazol-4-yl)acetate

Product 1

HCID 53983477HCID 53983477, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Pulverized potassium carbonate (0.33 g.) was suspended in a solution of ethyl 2-hydroxyimino-2-(2-methyl-1,3-thiazol-4-yl)acetate (syn isomer) (0.5 g.) in acetone (20 ml.). A solution of dimethyl sulfate (0.3 g.) in acetone (5 ml.) was dropwise added thereto with stirring at 40° to 45° C. After stirring for 2 hours at the same temperature, an insoluble material was filtered off. The filtrate was concentrated and water was added to the residue. The resulting mixture was extracted with ethyl acetate. The extract was in turn washed with water, a sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give pale yellow oil of ethyl 2-methoxyimino-2-(2-methyl-1,3-thiazol-4-yl)acetate (syn isomer) (0.5 g.).

Workup

  1. stirringAfter stirring for 2 hours at the same temperature
  2. filtrationan insoluble material was filtered off
  3. concentrationThe filtrate was concentrated
  4. additionwater was added to the residue
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materiala sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1a80a52ff4554914ab5ebecf772d4c7c
Source dataset
uspto-grants-1985_10
Patent number
US04544653

Reaction notes

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