Hydrochloric Acid → HCID 13934064, compound

HRID 2291937Notes

Reaction equation

HRID 2291937 reaction equation
N1C=CC=CC=1.[CH2:7]([N:13]([CH2:27][CH2:28][OH:29])[S:14]([C:17]1[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)(=[O:16])=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.Cl>C(Cl)(Cl)Cl>[CH2:7]([N:13]([CH2:27][CH2:28][O:29][S:36]([C:33]1[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=1)(=[O:38])=[O:37])[S:14]([C:17]1[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)(=[O:16])=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 13934063HCID 13934063, compound

Product 1

HCID 13934064HCID 13934064, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To 70 ml of pyridine were added 5.24 g of N-hexyl-N-(2-hydroxyethyl)-5-isoquinolinesulfonamide and 3.39 g of p-toluenesulfonyl chloride. The resulting mixture was stirred at 60° C. for 4 hours. Then, the pyridine was removed under reduced pressure to obtain an oily residue. To the residue were added 50 ml of chloroform and 20 ml of an aqueous hydrochloric acid solution having a pH of 2, and the chloroform layer was dried with anhydrous magnesium sulfate. Then, the chloroform was removed under reduced pressure to obtain a residue. The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C-200, 100 g; solvent: a 3% methanol solution in chloroform) to obtain 2.60 g of N-hexyl-N-(2-p-toluenesulfonyloxyethyl)-5-isoquinolinesulfonamide.

Workup

  1. customThen, the pyridine was removed under reduced pressure
  2. customto obtain an oily residue
  3. dry with materialthe chloroform layer was dried with anhydrous magnesium sulfate
  4. customThen, the chloroform was removed under reduced pressure
  5. customto obtain a residue
  6. customThe residue thus obtained
  7. customwas subjected to purification by silica gel column chromatography (Wacogel C-200, 100 g

Sources & evidence

ORD record
ord-d52b55c64b5d4cda999205c42f214847
Source dataset
uspto-grants-1989_01
Patent number
US04798897

Reaction notes

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