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

HRID 1733679Notes

Reaction equation

HRID 1733679 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]>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

5

Reactant 3

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

Product 1

HCID 54531055Ethyl cyano{[(methanesulfonyl)oxy]imino}acetateYield 96.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Ethyl 2-hydroxyimino-2-cyanoacetate (7.1 g) and triethylamine (7.0 ml) are dissolved in benzene (50 ml). To the solution is added dropwise a solution of methanesulfonyl chloride (3.9 ml) in benzene (8 ml) with stirring under ice-cooling and the mixture is stirred at the temperature for 3 hours and then allowed to stand overnight. The reaction mixture is filtered to remove the precipitates and the filtrate is concentrated to give crystals of ethyl 2-methanesulfonyloxyimino-2-cyanoacetate (10.6 g; 96.3%), melting point: 79°-83° C. The product is recrystallized from benzene-petroleum ether to give crystals having a melting point of 79°-81.5° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at the temperature for 3 hours
  3. filtrationThe reaction mixture is filtered
  4. customto remove the
  5. customprecipitates
  6. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-81121cf1573a49b78b64620986449e04
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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