Water → HCID 178472915, compound

HRID 463390Notes

Reaction equation

HRID 463390 reaction equation
[OH:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:15])(=O)=O.O.[Cl-].[Na+]>C(Cl)(Cl)Cl>[OH:1][N:2]=[C:3]([C:9](=[O:11])[CH2:10][Cl:15])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 24648Sulfuryl chloride2×HCID 178472877HCID 178472877, compound

Product 1

HCID 178472915HCID 178472915, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 31.83 g) in chloroform (70 ml) was added dropwise sulfuryl chloride (29.7 g) over 6 minutes under ice-cooling, and the mixture was stirred for 4.5 hours at ambient temperature. The mixture was cooled to 7° C., and sulfuryl chloride (13.498 g) was further added thereto. The mixture was stirred at ambient temperature for overnight. After the reaction mixture was cooled with ice-water, chloroform (50 ml) and water (40 ml) were added thereto with stirring. The mixture was saturated with sodium chloride, and the organic layer was separated, washed with a saturated aqueous solution of sodium chloride (40 ml×2), dried over magnesium sulfate and then filtered. The filtrate was evaporated to give ethyl 2-hydroxyimino-3-oxo-4-chlorobutyrate (syn isomer), quantitatively.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was cooled to 7° C.
  3. stirringThe mixture was stirred at ambient temperature for overnight
  4. additionwere added
  5. stirringwith stirring
  6. customthe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride (40 ml×2)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-2fd23d6a03174dd39f61335b3fa90fdc
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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