Sodium Bicarbonate → HCID 13934063, compound

HRID 2291936Notes

Reaction equation

HRID 2291936 reaction equation
Cl.[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.[C:16](=[O:19])([O-])O.[Na+]>>[CH2:2]([N:3]([CH2:4][CH2:16][OH:19])[S:12]([C:7]1[C:6]2[CH:5]=[CH:4][N:3]=[CH:2][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=[O:14])=[O:13])[CH2:11][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 13116932Isoquinoline-5-sulfonyl chloride hydrochloride

Product 1

HCID 13934063HCID 13934063, compound

Procedure

In 100 ml of ice water was dissolved 10.56 g of 5-isoquinolinesulfonyl chloride hydrochloride, and the pH of the solution was adjusted to 6 with a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with 100 ml of dichloromethane. The dichloromethane layer was added dropwise to a 100 ml of dichloromethane solution containing 8.7 g of N-hexylethanolamine and 6.1 g of triethylamine over 20 minutes while cooling with ice. The mixture was stirred at a temperature of 15° C. to 20° C. for 3 hours, washed with water, and dried with anhydrous magnesium sulfate. Then, thedichloromethane was removed under reduced pressure to obtain an oily residue. The thus obtained oily residue was subjected to purification by silica gel column chromatography (Wacogel C-200, 200 g; solvent: a 5% methanol solution in chloroform) to obtain 5.24 g of N-hexyl-N-(2-hydroxyethyl)-5-isoquinolinesulfonamide.

Workup

  1. extractionfollowed by extraction with 100 ml of dichloromethane
  2. additionThe dichloromethane layer was added dropwise to a 100 ml of dichloromethane solution
  3. additioncontaining 8.7 g of N-hexylethanolamine and 6.1 g of triethylamine over 20 minutes
  4. temperaturewhile cooling with ice
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThen, thedichloromethane was removed under reduced pressure
  8. customto obtain an oily residue
  9. customThe thus obtained oily residue was subjected to purification by silica gel column chromatography (Wacogel C-200, 200 g

Sources & evidence

ORD record
ord-27623f2a712b4ecf9d04d2eef2323e6f
Source dataset
uspto-grants-1989_01
Patent number
US04798897

Reaction notes

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