Sulfuryl chloride → HCID 49764778, compound

HRID 384993Notes

Reaction equation

HRID 384993 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][CH:4]([CH:6]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH2:8][S:7]1)[CH3:5].S(Cl)(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][CH:2]([CH3:14])[CH2:3][CH:4]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH3:5]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 49764776HCID 49764776, compound

Product 1

HCID 49764778HCID 49764778, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

After dissolving 2.8 g of 2-(4-methylpentan-2-yl)-3-nitro-2,5-dihydrothiophene in 40 ml of dichloromethane, a solution prepared by dissolving 2.6 g of sulfuryl chloride in 5 ml of dichloromethane was added thereto, and the solution was stirred at room temperature for 1.5 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 2.0 g of 2-(4-methylpentan-2-yl)-3-nitrothiophene (yield: 70.1%).

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-a4a47169d1bf4b3f929b39342d5733ff
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

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