Sodium Sulfite → HCID 86741673, compound

HRID 2118777Notes

Reaction equation

HRID 2118777 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[C:8]([O:11][CH:12]=[CH:13][CH2:14][CH2:15][CH3:16])(=[O:10])[CH3:9].C([O-])(O)=O.[Na+].[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl.O>[C:8]([O:11][C@@H:12]1[NH:5][C:6](=[O:7])[C@H:13]1[CH2:14][CH2:15][CH3:16])(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 53438372HCID 53438372, compound

Product 1

HCID 86741673HCID 86741673, compoundYield 3.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Eight hundred microliters of chlorosulfonyl isocyanate was added to a solution of 1.28 g (10 mM) pent-1-enyl acetate in 5 ml methylene chloride at 0° under nitrogen. After stirring at 0° 5 days, the reaction mixture was added dropwise to a mixture of 5 g ice, 1.15 ml water, 2.82 g NaHCO3 and 1.0 g Na2SO3 and stirred at 0° for 30 minutes. The mixture was extracted with 2×25 ml methylene choride and the combined organic phases washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel in hexane/ethyl acetate to yield 60 mg trans 4-acetoxy-3-n-propylazetidin-2-one (3.4%).

Workup

  1. stirringstirred at 0° for 30 minutes
  2. extractionThe mixture was extracted with 2×25 ml methylene choride
  3. washthe combined organic phases washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel in hexane/ethyl acetate

Sources & evidence

ORD record
ord-6ff696ffc96b4890b38645e5a4c33203
Source dataset
uspto-grants-1987_07
Patent number
US04680391

Reaction notes

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