Phosphorus pentachloride → 5-Isoquinolinesulfonyl chloride

HRID 442966Notes

Reaction equation

HRID 442966 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([OH:14])(=O)=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:16]>P(Cl)(Cl)(Cl)=O.C(Cl)(Cl)Cl>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([Cl:16])(=[O:14])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 2415995-Isoquinolinesulfonic acid

Product 1

HCID 33716555-Isoquinolinesulfonyl chlorideYield 96.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-isoquinolinesulfonic acid (4.18 g, 20 mmol), and phosphorus pentachloride (6.24 g, 30 mmol) in phosphorus oxychloride (20 mL) was heated at 120° C. for two days. The reaction mixture was cooled to ambient temperature and diluted with dry chloroform (60 mL). The white precipitate was collected, washed with dry chloroform and dried under high vacuum to give the title compound as a white solid (4.40 g, 83%) which was used for the next step without further purification. 1H-NMR (300 MHz, CDCl3) δ 9.95 (s, 1H), 9.16 (d, J=6.8 Hz, 1H), 8.74 (d, J=6.8 Hz, 1H), 8.52 (t, J=7.0 Hz, 2H), 7.99 (t, J=7.3 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe white precipitate was collected
  3. washwashed with dry chloroform
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-2e98cedbb9394ff2a70bcad0b90761e3
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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