Sulfuryl chloride → HCID 178501739, compound

HRID 621053Notes

Reaction equation

HRID 621053 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 19.6 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 as 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-0dc6aa10689b4066bc3af53e0328d40c
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

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