4-Toluenesulfonyl chloride → Ethyl 2-(p-toluenesulfonyloxyimino)-2-cyanoacetate

HRID 1733697Notes

Reaction equation

HRID 1733697 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.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(OCC)(=O)C>[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([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])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 2786718Ethyl 2-(p-toluenesulfonyloxyimino)-2-cyanoacetateYield 94.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In ethyl acetate (50 ml) are dissolved ethyl 2-hydroxyimino-2-cyanoacetate (7.1 g) and triethylamine (7.0 ml). To the solution is added p-toluenesulfonyl chloride (9.5 g) with stirring under ice-cooling, and the mixture is stirred for 2 hours and allowed to stand overnight. The reaction mixture is filtered and the filtrate is concentrated. To the residue is added cyclohexane and the resulting crystals are separated by filtration and dried to give ethyl 2-(p-toluenesulfonyloxyimino)-2-cyanoacetate (13.9 g), melting point: 84°-87° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for 2 hours
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. additionTo the residue is added cyclohexane
  6. customthe resulting crystals are separated by filtration
  7. customdried

Sources & evidence

ORD record
ord-ed8de17339a54d088ea496bb8e14f70e
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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