Chlorosulfonyl isocyanate → (2RS,3RS)-2,3-Diethyl-4-oxoazetidine-1-sulfonyl Chloride

HRID 335343Notes

Reaction equation

HRID 335343 reaction equation
[Cl:1][S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH3:8][CH2:9]/[CH:10]=[CH:11]/[CH2:12][CH3:13]>C(Cl)Cl>[CH2:9]([CH:10]1[CH:11]([CH2:12][CH3:13])[C:6](=[O:7])[N:5]1[S:2]([Cl:1])(=[O:4])=[O:3])[CH3:8]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 638066trans-3-Hexene

Product 1

HCID 14190960(2RS,3RS)-2,3-Diethyl-4-oxoazetidine-1-sulfonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chlorosulfonylisocyanate (5.17 ml, 59.4 mmol) in DCM (12 ml) was stirred at 25° C. and treated dropwise with (E)-hex-3-ene (7.39 ml, 59.4 mmol) in DCM (6 ml). The mixture was stirred at RT for 72 hrs. The reaction mixture was heated over 6 hrs at 40° C., before being poured onto ice. The mixture was extracted with DCM (3×100 ml) and the combined organics were washed with water (×1), dried MgSO4 and evaporated to dryness to afford the title compound;

Workup

  1. temperatureThe reaction mixture was heated over 6 hrs at 40° C.
  2. additionbefore being poured onto ice
  3. extractionThe mixture was extracted with DCM (3×100 ml)
  4. washthe combined organics were washed with water (×1), dried MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-95a0af855a8443f7a98d8e32b9cc1d39
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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