Sulfuryl chloride → HCID 178501739, compound

HRID 2231590Notes

Reaction equation

HRID 2231590 reaction equation
[OH:1][N:2]=[C:3]([C:8]([CH3:10])=[O:9])[C:4]([O:6][CH3:7])=[O:5].S(Cl)([Cl:14])(=O)=O>C(Cl)Cl>[Cl:14][CH2:10][C:8](=[O:9])[C:3](=[N:2][OH:1])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178501737HCID 178501737, compound

Product 1

HCID 178501739HCID 178501739, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of methylene chloride is dissolved 19 g of methyl 2-hydroxyiminoacetoacetate and under ice-cooling and stirring 1906 g of sulfuryl chloride is added dropwise. The mixture is stirred at room temperature for 3 days, after which the methylene chloride is distilled off under reduced pressure. The residue is dissolved in 200 ml of ether and washed seven times with 100 ml portions of water. The ether layer is dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 20.2 g of methyl 4-chloro-2-hydroxyiminoacetoacetate at a light-yellow oil.

Workup

  1. temperatureunder ice-cooling
  2. additionis added dropwise
  3. distillationafter which the methylene chloride is distilled off under reduced pressure
  4. dissolutionThe residue is dissolved in 200 ml of ether
  5. washwashed seven times with 100 ml portions of water
  6. dry with materialThe ether layer is dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5403745101f54f3db1e135847ac7de43
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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