Saccharin → Pseudosaccharin chloride

HRID 1819564Notes

Reaction equation

HRID 1819564 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 recrystallized 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. customrecrystallized from 60 mL toluene

Sources & evidence

ORD record
ord-2cac5dc93faf4a4e83ee856953f80d19
Source dataset
uspto-grants-2009_10
Patent number
US07601749B2

Reaction notes

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