Thionyl Chloride → 1-Chloroisoquinoline-5-sulfonyl chloride hydrochloride

HRID 2118499

Reaction equation

HRID 2118499 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([S:16]([OH:19])(=O)=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1>CN(C)C=O>[ClH:3].[Cl:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([S:16]([Cl:3])(=[O:19])=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 137300201-Chloroisoquinoline-5-sulfonic acid

Product 1

HCID 219799361-Chloroisoquinoline-5-sulfonyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 40 ml of thionyl chloride were added 2.93 g of 1-chloro-5-isoquinolinesulfonic acid as obtained in Example 1 and 0.4 ml of N,N-dimethylformamide. Then, the resulting mixture was refluxed while heating at 80° to 85° C. for 2 hours, followed by removal of the thionyl chloride under reduced pressure. Subsequently, 10 ml of dichloromethane was added to the reaction mixture to precipitate crystals, followed by separation of the crystals by filtration. The crystals thus obtained were washed with 10 ml of dichloromethane, and then dried under reduced pressure to obtain 3.06 g of 1-chloro-5-isoquinolinesulfonyl chloride hydrochloride. The compound was analyzed to give the following data.

Workup

  1. temperatureThen, the resulting mixture was refluxed
  2. temperaturewhile heating at 80° to 85° C. for 2 hours
  3. customfollowed by removal of the thionyl chloride under reduced pressure
  4. additionSubsequently, 10 ml of dichloromethane was added to the reaction mixture
  5. customto precipitate crystals
  6. customfollowed by separation of the crystals by filtration
  7. customThe crystals thus obtained
  8. washwere washed with 10 ml of dichloromethane
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-63a1456ec45c4ca2a3dd72572ef1f150
Source dataset
uspto-grants-1987_07
Patent number
US04678783

Linked notes

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