Sulfuryl chloride → HCID 49764777, compound

HRID 384992Notes

Reaction equation

HRID 384992 reaction equation
[N+:1]([C:4]1[CH:5]([CH:9]([CH2:11][CH2:12][CH3:13])[CH3:10])[S:6][CH2:7][CH:8]=1)([O-:3])=[O:2].S(Cl)(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[N+:1]([C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH:9]([CH2:11][CH2:12][CH3:13])[CH3:10])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 49764775HCID 49764775, compound

Product 1

HCID 49764777HCID 49764777, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

After dissolving 78 mg of 3-nitro-2-(pentan-2-yl)-2,5-dihydrothiophene in 2 ml of dichloromethane, a solution prepared by dissolving 78 mg of sulfuryl chloride in 2 ml of dichloromethane was added thereto, and the solution was stirred at room temperature for 2.5 hours. After adding an aqueous solution of saturated sodium bicarbonate, the solution was extracted with dichloromethane. The organic layer was washed with saturated saline, dried with magnesium sulfate and concentrated, and then purified by NH-silica gel chromatography (hexane/ethyl acetate=10/1), thereby obtaining 69 mg of 3-nitro-2-(pentan-2-yl)thiophene (yield: 88.7%).

Workup

  1. customa solution prepared
  2. additionwas added
  3. extractionthe solution was extracted with dichloromethane
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. custompurified by NH-silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-03459c1e90d540f6b969cc8b2b032e55
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

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