Sulfuryl chloride → Ethyl 4-chloro-3-oxo-2-(propoxyimino)butanoate

HRID 848250Notes

Reaction equation

HRID 848250 reaction equation
[O:1]=[C:2]([CH3:14])[C:3](=[N:9][O:10][CH2:11][CH2:12][CH3:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:18])(=O)=O>C(O)(=O)C>[Cl:18][CH2:14][C:2](=[O:1])[C:3](=[N:9][O:10][CH2:11][CH2:12][CH3:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 54491732Ethyl 3-oxo-2-(propoxyimino)butanoate

Product 1

HCID 53923607Ethyl 4-chloro-3-oxo-2-(propoxyimino)butanoateYield 85.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 3-oxo-2-propoxyiminobutyrate (syn isomer, 15.4 g.) and sulfuryl chloride (10.6 g.) were dissolved in acetic acid (15.4 ml.), warmed at 35° to 45° C. for 10 minutes with stirring and then stirred at ambient temperature for additional 6 hours. The reaction mixture was poured into ice-water (200 ml.) and the resultant mixture was extracted twice with chloroform. The extract was washed with an aqueous solution of sodium chloride, twice a saturated aqueous solution of sodium bicarbonate and once with water in turn, dried over magnesium sulfate, and then evaporated to dryness under reduced pressure to give ethyl 4-chloro-3-oxo-2-propoxyiminobutyrate (syn isomer, 15.4 g.), oil.

Workup

  1. temperaturewarmed at 35° to 45° C. for 10 minutes
  2. stirringstirred at ambient temperature for additional 6 hours
  3. extractionthe resultant mixture was extracted twice with chloroform
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialtwice a saturated aqueous solution of sodium bicarbonate and once with water in turn, dried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-eed38966fb844a228579db43b09ec00d
Source dataset
uspto-grants-1981_10
Patent number
US04294960

Reaction notes

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