Phosgene → 2-Chloro-3-pyridinesulfonylisocyanate

HRID 1759137Notes

Reaction equation

HRID 1759137 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 were 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 was removed in vacuo to yield 2-chloro-3-pyridinesulfonylisocyanate as an oil Bp 108°-110° (0.7 mm Hg). This product showed 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 was removed in vacuo

Sources & evidence

ORD record
ord-42504c8b92d14a40ab4ad46c7d08bd7a
Source dataset
uspto-grants-1982_07
Patent number
US04339267

Reaction notes

Loading…