Sulfuryl chloride → HCID 54469904, compound

HRID 745398Notes

Reaction equation

HRID 745398 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][N:8]=[C:9]([C:15](=[O:17])[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.S(Cl)([Cl:23])(=O)=O>C(O)(=O)C>[Cl:23][CH2:16][C:15](=[O:17])[C:9](=[N:8][O:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:19][CH:18]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 53716239HCID 53716239, compound

Product 1

HCID 54469904HCID 54469904, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 2-(4-methylbenzyloxyimino)-3-oxobutyrate (syn isomer, 74.08 g.), sulfuryl chloride (41.70 g.) and acetic acid (75 ml.) was stirred at at 40° to 42° C. for 4 hours. Nitrogen gas was bubbled into the reaction mixture. After adding the mixture into ice water, the mixture was extracted with methylene chloride. The extract was washed with sodium bicarbonate saturated aqueous solution and sodium chloride saturated aqueous solution in turn and dried over magnesium sulfate. After removing the solvent in vacuo, the residue was allowed to stand in a refrigerator overnight. The precipitates were removed by filtration, and the filtrate was concentrated in vacuo. The residue was subjected to column chromatography on silica gel and eluted with benzene and ethyl acetate. The eluate was concentrated in vacuo to give ethyl 4-chloro-2-(4-methylbenzyloxyimino)-3-oxobutyrate (syn isomer, 19.9 g.). I.R. νmaxFilm : 3000, 2950, 1740, 1710, 1600, 1440, 1400, 1370, 1340, 1270, 1200, 1000 cm-1.

Workup

  1. customNitrogen gas was bubbled into the reaction mixture
  2. additionAfter adding the mixture into 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 materialdried over magnesium sulfate
  6. customAfter removing the solvent in vacuo
  7. customto stand in a refrigerator overnight
  8. customThe precipitates were removed by filtration
  9. concentrationthe filtrate was concentrated in vacuo
  10. washeluted with benzene and ethyl acetate
  11. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-14aa0574f5834770a3757e995b33cade
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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