Phosgene → 2-Chloro-3-pyridinesulfonylisocyanate

HRID 2295249Notes

Reaction equation

HRID 2295249 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-2e145d4127e149cc899d0287e6686521
Source dataset
uspto-grants-1984_01
Patent number
US04424073

Reaction notes

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