Saccharin → Pseudosaccharin chloride

HRID 750622Notes

Reaction equation

HRID 750622 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].O1CCOCC1.S(Cl)([Cl:21])=O>CN(C=O)C>[Cl:21][C:5]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[S:1](=[O:3])(=[O:2])[N:4]=1

Participants

5

Reactant 3

HCID 5143SaccharinHCID 24386Thionyl ChlorideHCID 312751,4-Dioxane

Product 1

HCID 64783Pseudosaccharin chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Saccharin (10 g) was treated sequentially with dioxane (40 mL), thionyl chloride (15 mL) and DMF (0.4 mL). The resulting suspension was heated to reflux for 24 hours. The reaction mixture was concentrated to dryness and recrystalized from 60 mL toluene to give 5.7 g of the sub-title compound as a white solid.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 24 hours
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customrecrystalized from 60 mL toluene

Sources & evidence

ORD record
ord-6e8a0fd82837457fa54d7a8953df5c6a
Source dataset
uspto-grants-2008_07
Patent number
US07405215B2

Reaction notes

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