Thionyl Chloride → Isoquinoline-5-sulfonyl chloride hydrochloride

HRID 2118497Notes

Reaction equation

HRID 2118497 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.S(Cl)([Cl:17])=O>>[ClH:17].[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([Cl:17])(=[O:14])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2415995-Isoquinolinesulfonic acid

Product 1

HCID 13116932Isoquinoline-5-sulfonyl chloride hydrochloride

Procedure

To 1200 ml of thionyl chloride were added 150 g of 5-isoquinolinesulfonic acid and 0.4 ml of N,Ndimethylformamide. Then, the resulting mixture was refluxed while heating at 80° to 85 ° C for 3 hours, followed by removal of the thionyl chloride under reduced pressure. Subsequently, 300 ml of dichloromethane was added to the reaction mixture to precipitate crystals. The precipitated crystals were separated by filtration, washed with 100 ml of dichloromethane, and then dried under reduced pressure to obtain 170 g of 5-isoquinolinesulfonyl chloride hydrochloride.

Workup

  1. temperatureThen, the resulting mixture was refluxed
  2. temperaturewhile heating at 80° to 85 ° C for 3 hours
  3. customfollowed by removal of the thionyl chloride under reduced pressure
  4. additionSubsequently, 300 ml of dichloromethane was added to the reaction mixture
  5. customto precipitate crystals
  6. customThe precipitated crystals were separated by filtration
  7. washwashed with 100 ml of dichloromethane
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-1c9cce957c6541c6bad7e27fdb0e10ea
Source dataset
uspto-grants-1987_07
Patent number
US04678783

Reaction notes

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