Dimethyl Sulfate → Tert-butyl 2-methoxyimino-3-phenyliminobutyrate

HRID 1614078Notes

Reaction equation

HRID 1614078 reaction equation
[OH:1][N:2]=[C:3]([C:11](=[N:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:20](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:20][O:1][N:2]=[C:3]([C:11](=[N:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:12])[C:4]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 136404523Tert-butyl 2-hydroxyimino-3-phenyliminobutyrate

Product 1

HCID 54521467Tert-butyl 2-methoxyimino-3-phenyliminobutyrateYield 64.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of tert-butyl 2-hydroxyimino-3-phenyliminobutyrate (1.0 g) in acetone (10 ml) was added potassium carbonate (0.63 g) and dimethyl sulfate (0.43 ml) under ice-cooling. The mixture was stirred at the same temperature for 30 minutes and stirred at ambient temperature for 4 hours. The resulting suspension was poured into ice-water and extracted with diisopropyl ether. The organic layer was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residual oil was subjected to column chromatography on silica gel give tert-butyl 2-methoxyimino-3-phenyliminobutyrate (0.68 g).

Workup

  1. temperaturecooling
  2. stirringstirred at ambient temperature for 4 hours
  3. extractionextracted with diisopropyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-27208230ae22427b919756e2c1ccecdc
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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