HCID 53896826, compound → Saccharin

HRID 864765Notes

Reaction equation

HRID 864765 reaction equation
C([N:5]1[C:9](=[O:10])[C:8]2[CH:11]3C[CH:14]([C:7]=2[S:6]1(=[O:17])=[O:16])[CH2:13][CH2:12]3)(C)(C)C>FC(F)(F)C(O)=O>[S:6]1([C:7]2[C:8](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:10])[NH:5]1)(=[O:16])=[O:17]

Participants

3

Reactant 1

HCID 53896826HCID 53896826, compound

Product 1

HCID 5143Saccharin

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The 2-t-butyl-4,5,6,7-tetrahydro-4,7-methano-1,2-benzisothiazol-3(2H)one 1,1-dioxide (2.8 g, 0.011 mol) in trifluoroacetic acid (30 mL) was heated at reflux for 48 hr and let stand at room temperature for 4 days. The resulting mixture was concentrated in vacuo, treated with methanol (20 mL) and evaporated to dryness. The residue was taken up in ether (100 mL) and washed with saturated NaHCO3 (1×50 mL). The layers were separated, the aqueous phase acidified to pH 1 with 2N HCl and extracted with MDC (2×100 mL). The combined organic extracts were dried and concentrated in vacuo to give 0.9 g (42%) of the bicyclo (2.2.1) saccharin derivative as a white solid.

Workup

  1. temperatureat reflux for 48 hr
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. additiontreated with methanol (20 mL)
  4. customevaporated to dryness
  5. washwashed with saturated NaHCO3 (1×50 mL)
  6. customThe layers were separated
  7. extractionextracted with MDC (2×100 mL)
  8. customThe combined organic extracts were dried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3c530be0e6a432f955bbabb837226e0
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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