Benzisothiazole → HCID 83678697, compound

HRID 514828

Reaction equation

HRID 514828 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[N:2]1.[Cl:10][S:11](O)(=[O:13])=[O:12]>>[S:1]1[C:5]2[C:6]([S:11]([Cl:10])(=[O:13])=[O:12])=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[N:2]1

Participants

3

Reactant 2

HCID 9225BenzisothiazoleHCID 24638Chlorosulfonic acid

Product 1

HCID 83678697HCID 83678697, compoundYield 15.6%

Procedure

Benzo[d]isothiazole 24B (1 g, 7.45 mmol) was added dropwise to chlorosulfonic acid (5.5 mmol) at 0° C. After the addition was complete, the mixture was stirred at room temperature for 0.5 h and then heated at 105° C. and stirred overnight. The resulting mixture was cooled to −10° C. and quenched by pouring on crushed ice slowly. The resulting mixture was extracted with EtOAc (100 mL×2). The combined organic phase was washed with brine, dried over anhy. Na2SO4 and concentrated in vacuo. Column chromatography (15% PE/EtOAc) afforded 200 mg of title compound. 1H NMR (CHLOROFORM-d) δ: 9.68 (s, 1H), 8.66 (d, J=1.9 Hz, 1H), 8.10 (d, J=9.4 Hz, 1H), 7.99 (dd, J=9.4, 2.1 Hz, 1H).

Workup

  1. additionAfter the addition
  2. temperatureheated at 105° C.
  3. stirringstirred overnight
  4. temperatureThe resulting mixture was cooled to −10° C.
  5. customquenched
  6. additionby pouring
  7. customon crushed ice slowly
  8. extractionThe resulting mixture was extracted with EtOAc (100 mL×2)
  9. washThe combined organic phase was washed with brine
  10. customdried over anhy
  11. concentrationNa2SO4 and concentrated in vacuo

Sources & evidence

ORD record
ord-17b817ca05ae4827a22c9262b1aa6343
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Linked notes

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