Saccharin → 2-Cyanobenzenesulfonyl Chloride

HRID 1090364Notes

Reaction equation

HRID 1090364 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=O)[NH:4]1)(=[O:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)[Cl:14]>O>[C:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=1[S:1]([Cl:14])(=[O:3])=[O:2])#[N:4]

Participants

4

Reactant 2

HCID 5143SaccharinHCID 24819Phosphorus pentachloride

Product 1

HCID 5223472-Cyanobenzenesulfonyl ChlorideYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

44 grams(0.24 mole) of saccharin and 100 grams(0.48 mole) of phosphorus pentachloride were stirred at 110° C. to 120° C. for 3.5 hours. The reaction mixture was then poured into 500 milliliters of ice and water, stirred until solidified, filtered, ground with water, re-filtered, and dried to give 44.3 grams of 2-cyanobenzenesulfonyl chloride and pseudosaccharin chloride. Based on saccharin, the per cent yield was 92.

Workup

  1. filtrationfiltered
  2. filtrationground with water, re-filtered
  3. customdried

Sources & evidence

ORD record
ord-ee7e1f4ff51f44e9a44ca97e3a23ae72
Source dataset
uspto-grants-1992_01
Patent number
US05081275

Reaction notes

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