Saccharin → Pseudosaccharin chloride

HRID 2243208Notes

Reaction equation

HRID 2243208 reaction equation
[O:1]=[S:2]1(=[O:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=O)[NH:3]1.S(Cl)([Cl:15])=O>O1CCOCC1.CN(C=O)C>[Cl:15][C:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[S:2](=[O:12])(=[O:1])[N:3]=1

Participants

5

Reactant 2

HCID 5143SaccharinHCID 24386Thionyl Chloride

Product 1

HCID 64783Pseudosaccharin chlorideYield 77.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 312751,4-DioxaneSolvent

Procedure

step 4—To a solution of saccharin (25, 5.0 g, 27 mmol) in dioxane (100 mL) was added thionyl chloride (3.0 mL, 41 mmol) and DMF (5 drops). The reaction mixture was heated at reflux for 2 d, and the lightly colored solution was cooled to RT. The solvent was removed in vacuo to afford 4.2 g of 26 as an off-white solid that was recrystallized from toluene: LCMS RT 2.6 min, M+H.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 d
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aad888c2cf0d42feabe428d724857e27
Source dataset
uspto-grants-2010_03
Patent number
US07674810B2

Reaction notes

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