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

HRID 1733680Notes

Reaction equation

HRID 1733680 reaction equation
[OH:1][N:2]=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>C1C=CC=CC=1>[CH3:18][S:19]([O:1][N:2]=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 54531055Ethyl cyano{[(methanesulfonyl)oxy]imino}acetateYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

Ethyl 2-hydroxyimino-2-cyanoacetate (28.4 g) and triethylamine (28.0 ml) are dissolved in benzene (150 ml). To the solution is added dropwise a solution of methanesulfonyl chloride (15.6 ml) in benzene (40 ml) with stirring under ice-cooling. After allowing to stand overnight, to the reaction mixture are added benzene (500 ml) and water (100 ml). The benzene layer is washed with water and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off and the residue is washed well with ether and petroleum ether to give ethyl 2-methane-sulfonyloxyimino-2-cyanoacetate (41.8 g; 95%), melting point: 78°-81° C.

Workup

  1. temperaturecooling
  2. washThe benzene layer is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter drying
  5. distillationthe solvent is distilled off
  6. washthe residue is washed well with ether and petroleum ether

Sources & evidence

ORD record
ord-af0d317cb8a744259379998f5f29a35b
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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