Sulfuryl chloride → HCID 53707812, compound

HRID 745402Notes

Reaction equation

HRID 745402 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:24]=[CH:23][C:10]([CH2:11][O:12][N:13]=[C:14]([C:20](=[O:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1>C(O)(=O)C>[Cl:4][CH2:21][C:20](=[O:22])[C:14](=[N:13][O:12][CH2:11][C:10]1[CH:9]=[CH:8][C:7]([Cl:6])=[CH:24][CH:23]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 54496467HCID 54496467, compound

Product 1

HCID 53707812HCID 53707812, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfuryl chloride (39.26 g.) was added to a solution of ethyl 2-(4-chlorobenzyloxyimino)-3-oxobutyrate (syn isomer, 75.03 g.), in acetic acid (75 ml.), and then stirred at 37° to 40° C. for 8 hours. After air was bubbled into the reaction mixture, the mixture was added to ice water. The mixture was extracted with methylene chloride, and the extract was washed with sodium bicarbonate saturated aqueous solution and sodium chloride saturated aqueous solution in turn. The solution was dried over magnesium sulfate and concentrated in vacuo to give ethyl 4-chloro-2-(4-chlorobenzyloxyimino)-3-oxobutyrate (syn isomer, 77.23 g.).

Workup

  1. customAfter air was bubbled into the reaction mixture
  2. additionthe mixture was added to ice water
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe extract was washed with sodium bicarbonate saturated aqueous solution and sodium chloride saturated aqueous solution in turn
  5. dry with materialThe solution was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24f7d9fa422d42db9a70799bc8631d44
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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