Thionyl Chloride → Benzenesulfonyl isocyanate, 2-chloro-

HRID 1980084Notes

Reaction equation

HRID 1980084 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].S(Cl)(Cl)=O.Cl[C:17](SCl)=[O:18]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]=[C:17]=[O:18])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 75990(Chlorothio)formyl chlorideHCID 814102-Chlorobenzenesulfonamide

Product 1

HCID 174071Benzenesulfonyl isocyanate, 2-chloro-

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

In a flask equipped with a stirrer, reflux condenser and nitrogen bubbling apparatus, were mixed 5 g (0.03 mole) o-chlorobenzenesulfonamide, 50 ml (0.686 mole) thionyl chloride and 2 drops of pyridine. Then 3.9 g (0.03 mole) chlorocarbonylsulfenyl chloride was slowly added.

Workup

  1. customIn a flask equipped with a stirrer
  2. temperaturereflux condenser

Sources & evidence

ORD record
ord-0c0fb5ab8441446fa39bef89df1cf700
Source dataset
uspto-grants-1984_11
Patent number
US04485053

Reaction notes

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