Benzothiazole → 1,3-Benzothiazole-4-sulfonyl chloride

HRID 2202362Notes

Reaction equation

HRID 2202362 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Cl:10][S:11](O)(=[O:13])=[O:12]>>[S:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([S:11]([Cl:10])(=[O:13])=[O:12])=[C:4]2[N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 7222BenzothiazoleHCID 24638Chlorosulfonic acid

Product 1

HCID 149512121,3-Benzothiazole-4-sulfonyl chlorideYield 17%

Procedure

Benzo[d]thiazole (1 g, 7.45 mol) 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 218 mg of title compound. 1H NMR (CHLOROFORM-d) δ: 9.41 (s, 1H), 8.41 (dd, J=8.1, 1.0 Hz, 1H), 8.29 (dd, J=7.7, 1.1 Hz, 1H), 7.68 (t, J=7.9 Hz, 1H). LC-MS: m/z 234.7 (M+H)+

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-c81afb7dd7cd414e9531edf8be8d51ab
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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