Sulfuryl chloride → HCID 88627674, compound

HRID 1194873Notes

Reaction equation

HRID 1194873 reaction equation
[CH:1]1([O:7]/[N:8]=[C:9](/[C:15](=[O:17])[CH3:16])\[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:21])(=O)=O>>[Cl:21][CH2:16][C:15](=[O:17])/[C:9](=[N:8]/[O:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 14864954HCID 14864954, compound

Product 1

HCID 88627674HCID 88627674, compoundYield 60%

Procedure

Ethyl (Z)-2-(cyclohexyloxyimino)-3-oxobutyrate (1.0 g) was added to ice-cooled sulphuryl chloride (10 ml) with stirring. The mixture was allowed to warm to room temperature, stirred for 27 h, then evaporated under an argon stream. The residue was dissolved in diethyl ether, washed twice with water, then brine, dried (MgSO4) and evaporated. Purification by flash chromatography, eluting with dichloromethane/carbon tetrachloride gave the title compound (0.69 g, 60%) as a colourless liquid; νmax (film) 2950, 2860, 1750, 1720 cm-1 ; δH (CDCl3) 1.32 (3H, t), 1.2-2.0 (10H, br m), 4.3 (1H, br m), 4.34 (2H, q), and 4.53 (2H, s), (Found: MH+ 276.0998, C12H18NO4Cl requires M+H 276.1004).

Workup

  1. stirringstirred for 27 h
  2. customevaporated under an argon stream
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwashed twice with water
  5. dry with materialbrine, dried (MgSO4)
  6. customevaporated
  7. customPurification by flash chromatography
  8. washeluting with dichloromethane/carbon tetrachloride

Sources & evidence

ORD record
ord-f5a7d60134b441b4a2803f4fd049c1b2
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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