Dimethyl Sulfate → HCID 86759322, compound

HRID 1840671Notes

Reaction equation

HRID 1840671 reaction equation
C[C:2](=[O:9])[C:3](=NO)[C:4](=[O:6])[CH3:5].S([O:15][CH3:16])(OC)(=O)=O.[C:17](=O)([O-])[O-].[K+].[K+].[CH2:23]([NH:25][CH2:26]C)C>COC(C)(C)C.CN(C)C=O>[CH3:23][N:25]([CH:2]=[O:9])[CH3:26].[CH3:17][C:4]([O:15][CH3:16])([CH3:3])[CH3:5].[OH2:6]

Participants

7

Reactant 4

HCID 6497Dimethyl Sulfate2×HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 178468373HCID 178468373, compound

Product 1

HCID 86759322HCID 86759322, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 129 g of pentane-2,3,4-trione 3-oxime in 246 g of MTBE and 132 g of dimethyl sulfate (DMS) were added dropwise to 332 g of a 50% by weight aqueous solution of potassium carbonate, 110 g of dimethylformamide (DMF), 300 g of tert-butyl methyl ether (MTBE) and 7 g of dimethyl sulfate (DMS) at about 17-19° C. with cooling. After stirring at about 20° C. for 2 h, 36.5 g of diethylamine were added to destroy excess DMS and, after stirring at about 20° C. for a further hour, 600 ml of water were added. The solution was extracted with tert-butyl methyl ether. From the combined organic phases there were obtained after washing with 1 N H2SO4 136.9 g of pentane-2,3,4-trione 3-O-methyloxime (96.3% pure according to GC analysis), corresponding to a yield of 92.1% of theory.

Workup

  1. temperaturewith cooling
  2. customto destroy excess DMS
  3. stirringafter stirring at about 20° C. for a further hour
  4. addition600 ml of water were added
  5. extractionThe solution was extracted with tert-butyl methyl ether
  6. customFrom the combined organic phases there were obtained
  7. washafter washing with 1 N H2SO4 136.9 g of pentane-2,3,4-trione 3-O-methyloxime (96.3% pure according to GC analysis), corresponding to a yield of 92.1% of theory

Sources & evidence

ORD record
ord-0402ccff2e36456ca5e4f314c1518f79
Source dataset
uspto-grants-2004_01
Patent number
US06680410B2

Reaction notes

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