Phosgene → 2-Chloro-3-pyridinesulfonylisocyanate

HRID 1155940Notes

Reaction equation

HRID 1155940 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 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-635ba1a774914d31bb6bb41e0c9f243b
Source dataset
uspto-grants-1982_06
Patent number
US04333760

Reaction notes

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