Benzene → Ethyl cyano{[(methanesulfonyl)oxy]imino}acetate

HRID 1733681Notes

Reaction equation

HRID 1733681 reaction equation
[OH:1][N:2]=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].C1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>O>[CH3:23][S:24]([O:1][N:2]=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 54531055Ethyl cyano{[(methanesulfonyl)oxy]imino}acetateYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-hydroxyimino-2-cyanoacetate (28.4 g) and anhydrous potassium carbonate (13.8 g) are dissolved in water (100 ml) and thereto is added benzene (10 ml). To the mixture is added dropwise methanesulfonyl chloride (15.6 ml) with stirring under ice-cooling and the mixture is further stirred for 1 hour. After allowing to stand overnight, the reaction mixture is extracted with ethyl acetate (300 ml). The extract is washed with water and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off to give ethyl 2-methanesulfonyloxyimino-2-cyanoacetate (38.0 g; 86.3%), melting point: 79°-81° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is further stirred for 1 hour
  3. extractionthe reaction mixture is extracted with ethyl acetate (300 ml)
  4. washThe extract is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter drying
  7. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-ca28b3a8a450435684678af01b01c5f5
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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