Hydrochloric Acid → 5-Bromopyridine-3-sulphonic acid

HRID 839386Notes

Reaction equation

HRID 839386 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([OH:10])(=[O:9])=[O:8])[CH:2]=1.P(Cl)(Cl)(Cl)(Cl)Cl.Cl.[Br:18]Br>O.C(Cl)(Cl)Cl>[Br:18][C:5]1[CH:4]=[C:3]([S:7]([OH:10])(=[O:9])=[O:8])[CH:2]=[N:1][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 126842615-Bromopyridine-3-sulphonic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 3g. of 3-pyridinesulfonic acid and 8.5g. of phosphorous pentachloride was heated at 120° C for 1.5 hours. Upon cooling to room temperature, the mixture solidified. Chloroform was added thereto and dry hydrogen chloride gas was introduced. The resulting precipitate was collected by filtration and dried. The crystalline substance obtained was heated with bromine (4g.) at 120° C. for 8 hours and water (60 ml.) was added to the mixture. After stirring at 80° C. for 2 hours, the solution was concentrated. On addition of acetone, 2g. of 5-bromo- 3-pyridinesulfonic acid was obtained.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried
  3. customThe crystalline substance obtained
  4. concentrationthe solution was concentrated
  5. additionOn addition of acetone, 2g

Sources & evidence

ORD record
ord-fe469ed7e841436a912cd1202abd0cfd
Source dataset
uspto-grants-1978_06
Patent number
US04094982

Reaction notes

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