Hydrochloric Acid → Pyridine-3-sulfonyl chloride hydrochloride

HRID 842733Notes

Reaction equation

HRID 842733 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([OH:10])(=O)=[O:8])[CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12].[ClH:17]>P(Cl)(Cl)(Cl)=O>[ClH:12].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([Cl:17])(=[O:10])=[O:8])[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 12571517Pyridine-3-sulfonyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of pyridine-3-sulfonic acid (15.0 g), phosphorous pentachloride (24.0 g) and phosphorous oxychloride (30 mL) was heated to 120° C. for 16 h. The reaction was cooled to room temperature, and the resulting suspension was saturated with HCl (g). A white precipitate was collected, washed with CHCl3, and dried in vacuo to afford the title compound (15.6 g). 1H NMR (400 MHz, DMSO) δ 8.98 (s, 1H), 8.85 (d, 1H), 8.66 (d, 1H), 8.02 (t, 1H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customA white precipitate was collected
  3. washwashed with CHCl3
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4b081424180d4966bb8480490dbd0689
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

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