Phosphorus pentachloride → 5-Isoquinolinesulfonyl chloride

HRID 1977944Notes

Reaction equation

HRID 1977944 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 room 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 next step without further purification. 1H-NMR (300 MHz, CDCl3)δ9.95 (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 room temperature
  2. customThe white precipitate was collected
  3. washwashed with dry chloroform
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-ef11fe6cfad8490b90fbc1e151fc6c83
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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