Saccharin → 2-(1,3-Benzodioxol-5-ylmethyl)-1,1-dioxo-1,2-benzothiazol-3-one

HRID 1449537Notes

Reaction equation

HRID 1449537 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4]1)(=[O:3])=[O:2].[CH2:13]1[O:23][C:22]2[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][C:15]=2[O:14]1>CN(C=O)C.C(Cl)Cl.C(OCC)(=O)C>[O:23]1[C:22]2[CH:21]=[CH:20][C:17]([CH2:18][N:4]3[C:5](=[O:6])[C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=4[S:1]3(=[O:2])=[O:3])=[CH:16][C:15]=2[O:14][CH2:13]1

Participants

6

Reactant 2

HCID 5143SaccharinHCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Product 1

HCID 64639312-(1,3-Benzodioxol-5-ylmethyl)-1,1-dioxo-1,2-benzothiazol-3-one

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To saccharin (5.0 g, 0.0273 mol) in DMF (10 mL) was added Nail (1.15 g, 60% in oil, 0.0288 mol) with ice bath cooling. After stirring for 10 minutes. a solution of 3,4-methylenedioxybenzyl chloride in methylene chloride, 50% by weight, (10 g, 0.0293 mol) was added and the mixture stirred for 16 hours. The mixture was diluted with ethyl acetate (200 mL) containing 10% methylene chloride and washed with IN HCl (2×100 mL). The organic phase was washed with brine and dried over MgSO4. The mixture was concentrated until crystals were apparent. After standing for 16 hours the product was collected by filtration (4.2 g, 49%);

Workup

  1. temperaturecooling
  2. stirringthe mixture stirred for 16 hours
  3. washwashed with IN HCl (2×100 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationThe mixture was concentrated until crystals
  7. waitAfter standing for 16 hours
  8. filtrationthe product was collected by filtration (4.2 g, 49%)

Sources & evidence

ORD record
ord-f9e46906a401421eb678aa1853c7cd2d
Source dataset
uspto-grants-1997_02
Patent number
US05599811

Reaction notes

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