Phosgene → 2-Chloro-3-pyridinesulfonylisocyanate

HRID 66448Notes

Reaction equation

HRID 66448 reaction equation
[Cl:1][C:2]1[C:7]([S:8]([NH:11][C:12](=[O:18])NCCCC)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(Cl)(Cl)=O>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:7]([S:8]([N:11]=[C:12]=[O:18])(=[O:9])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 12383441HCID 12383441, compound

Product 1

HCID 130384352-Chloro-3-pyridinesulfonylisocyanate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 125 ml of dry xylene was added with stirring 20.7 g of 2-chloro-N-(butylcarbamoyl)-3-pyridinesulfonamide. This solution was heated to reflux, and phosgene added until no further uptake of this gas was observed. It was then cooled, filtered and the solvent removed in vacuo to yield 2-chloro-3-pyridinesulfonylisocyanate as an oil Bp 108°-110° (0.7 mm Hg) and showing a sharp absorption peak in the infrared region at 2220 cm-1.

Workup

  1. temperatureThis solution was heated
  2. temperatureto reflux
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cf633d82c853409d8f88604f2c144b40
Source dataset
uspto-grants-1982_08
Patent number
US04342587

Reaction notes

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