Phosgene → HCID 13645990, compound

HRID 280076Notes

Reaction equation

HRID 280076 reaction equation
[CH3:1][Se:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10].C(N=[C:18]=[O:19])CCC.C(Cl)(Cl)=O>>[CH3:1][Se:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]=[C:18]=[O:19])(=[O:11])=[O:10]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 13645989HCID 13645989, compound

Product 1

HCID 13645990HCID 13645990, compoundYield 127.5%

Procedure

A solution of 2-(methylselenyl)benzenesulfonamide (6.25 g, 25.0 mmol), n-butyl isocyanate (2.81 mL, 25.0 mmol), and 1,4-diaza[2.2.2]bicyclooctane (0.1 g, 1 mmol) in mixed xylenes was heated at reflux for 0.5 hours. Phosgene was then added at such a rate that the internal temperature stayed at 133° C. or above. When consumption of phosgene ceased, the solution was cooled to room temperature and then filtered under nitrogen. Rotary evaporation gave 2-(methylselenyl)benzenesulfonyl isocyanate as a brown oil (8.8 g). This was used immediately without further purification or characterization.

Workup

  1. temperatureat reflux for 0.5 hours
  2. customstayed at 133° C. or above
  3. customWhen consumption of phosgene
  4. filtrationfiltered under nitrogen
  5. customRotary evaporation

Sources & evidence

ORD record
ord-c812205a6af543fcaea77c3881533a83
Source dataset
uspto-grants-1986_05
Patent number
US04588432

Reaction notes

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