Phosgene → Sulphonyl diisocyanate

HRID 746151Notes

Reaction equation

HRID 746151 reaction equation
[NH2:1][S:2](C1C=C(C2C=CC=CC=2)C=CC=1C(OC)=O)(=[O:4])=[O:3].C1N2CCN(CC2)C1.C([N:33]=[C:34]=[O:35])CCC.[C:36](Cl)(Cl)=[O:37]>>[S:2]([N:1]=[C:36]=[O:37])([N:33]=[C:34]=[O:35])(=[O:3])=[O:4]

Participants

5

Reactant 4

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 9237DabcoHCID 13456737HCID 13456737, compound

Product 1

HCID 77898Sulphonyl diisocyanate

Procedure

The sulfonamide of Example 5 (5.0 g) was stirred in 75 mL dry xylenes with 0.1 g DABCO® and 1.9 mL n-butylisocyanate, then heated to reflux (138°) with a dry ice condenser in place. Phosgene gas was introduced into the vessel above the liquid level until the reaction temperature dropped below 130°. As phosgene was absorbed by the reactants, a gradual rise in reaction temperature was observed. Heating was continued until the reaction temperature remained constant, indicating complete consumption of the sulfonamide starting material (ca. 2 hrs). Evaporation of the xylenes after filtration under nitrogen to remove traces of solid gave crude sulfonyl isocyanate as a viscous oil, IR (neat) 2250 cm-1.

Workup

  1. temperatureheated
  2. temperatureto reflux (138°) with a dry ice condenser in place
  3. additiondropped below 130°
  4. customAs phosgene was absorbed by the reactants
  5. customa gradual rise in reaction temperature
  6. temperatureHeating
  7. customconsumption of the sulfonamide starting material (ca. 2 hrs)
  8. customEvaporation of the xylenes
  9. filtrationafter filtration under nitrogen
  10. customto remove traces of solid

Sources & evidence

ORD record
ord-704f24544a5f4fa19c33f1379593e84b
Source dataset
uspto-grants-1986_07
Patent number
US04602942

Reaction notes

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