Dimethylformamide → HCID 19007135, compound

HRID 2118501Notes

Reaction equation

HRID 2118501 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([S:16]([OH:19])(=[O:18])=O)[C:10]=2[CH:9]=[CH:8][N:7]=1.C[N:21]([CH3:24])C=O.[C:25](=O)([O-])[OH:26].[Na+]>O>[OH:26][CH2:25][CH2:24][NH:21][S:16]([C:11]1[C:10]2[CH:9]=[CH:8][N:7]=[C:6]([Cl:5])[C:15]=2[CH:14]=[CH:13][CH:12]=1)(=[O:18])=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 137300201-Chloroisoquinoline-5-sulfonic acid

Product 1

HCID 19007135HCID 19007135, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of thionyl chloride were added 5.85 g of 1-chloro-5-isoquinolinesulfonic acid as obtained in Example 1 and 0.5 ml of N,N-dimethylformamide. Then, the resulting mixture was refluxed while heating for 2 hours, followed by removal of the thionyl chloride and N,N-dimethylformamide under reduced pressure to obtain a residue. Then, the residue was dissolved in 50 ml of water, and the pH of the aqueous solution was adjusted to 6.0 with an aqueous sodium hydrogencarbonate saturated solution, followed by extraction twice with 50 ml of dichloromethane. The dichloromethane layer was added to a 50 ml of dichloromethane solution containing 1.84 g of ethanolamine and 3.03 g of triethylamine for 5 minutes while cooling with ice. Then, the mixture was stirred for 1 hour at a temperature of 10° C. to 20° C. The thus obtained reaction mixture was washed thrice with water, dried with anhydrous sodium sulfate and then distilled under reduced pressure to obtain 5.04 g of N-(2 -hydroxy- ethyl)-1-chloro-5-isoquinolinesulfonamide in a 96% yield.

Workup

  1. temperatureThen, the resulting mixture was refluxed
  2. temperaturewhile heating for 2 hours
  3. customfollowed by removal of the thionyl chloride and N,N-dimethylformamide under reduced pressure
  4. customto obtain a residue
  5. extractionfollowed by extraction twice with 50 ml of dichloromethane
  6. additionThe dichloromethane layer was added to a 50 ml of dichloromethane solution
  7. additioncontaining 1.84 g of ethanolamine and 3.03 g of triethylamine for 5 minutes
  8. temperaturewhile cooling with ice
  9. customThe thus obtained reaction mixture
  10. washwas washed thrice with water
  11. dry with materialdried with anhydrous sodium sulfate
  12. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-8ce6094d1eac4304b397a3c1aadc1670
Source dataset
uspto-grants-1987_07
Patent number
US04678783

Reaction notes

Loading…