Chlorosulfonic acid → HCID 90418911, compound

HRID 2202369Notes

Reaction equation

HRID 2202369 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>>[NH2:9][C:7]1[S:8][C:4]2[C:5](=[C:10]([S:13]([Cl:12])(=[O:15])=[O:14])[CH:11]=[C:2]([F:1])[CH:3]=2)[N:6]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 3199542-Amino-6-fluorobenzothiazole

Product 1

HCID 90418911HCID 90418911, compoundYield 15%

Procedure

6-fluorobenzo[d]thiazol-2-amine (1 g, 5.95 mol) was added dropwise to chlorosulfonic acid (5.0 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 (50% PE/EtOAc) afforded 200 mg of title compound. LC-MS: m/z 266.7 (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-d9a74515c4c545a29e079d817a5c71c8
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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