Pyridine → HCID 21278399, compound

HRID 2291954Notes

Reaction equation

[CH2:1]([N:3]([CH2:17][CH2:18][OH:19])[S:4]([C:7]1[C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1)(=[O:6])=[O:5])[CH3:2].N1C=CC=CC=1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>ClCCl>[CH2:1]([N:3]([CH2:17][CH2:18][O:19][S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)(=[O:34])=[O:33])[S:4]([C:7]1[C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1)(=[O:5])=[O:6])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To 5.77 g of N-ethyl-N-(2-hydroxyethyl)-5-isoquinolinesulfonamide were added 100 ml of pyridine and 4.0 g of p-toluenesulfonyl chloride. The mixture thus obtained was heated at 80° C. for 48 hours, and then the pyridine was removed under reduced pressure to obtain a residue. To the residue was added 100 ml of dichloromethane, and the resultant mixture was washed thrice with a hydrochloric acid solution having a pH of 5 and dried with anhydrous magnesium sulfate. Then, the dichloromethane was removed under reduced pressure to obtain a residue. The residue was subjected to purification by silica gel column chromatography (Wacogel C-200, solvent: a 5% methanol solution in chloroform) to obtain 3.96 g of N-ethyl-N-(2-p-toluenesulfonyloxyethyl)-5-isoquinolinesulfonamide.

Workup

customThe mixture thus obtained
customthe pyridine was removed under reduced pressure
customto obtain a residue
washthe resultant mixture was washed thrice with a hydrochloric acid solution
dry with materialdried with anhydrous magnesium sulfate
customThen, the dichloromethane was removed under reduced pressure
customto obtain a residue
customThe residue was subjected to purification by silica gel column chromatography (Wacogel C-200, solvent

Sources & evidence

ORD record: ord-1635336ccada40ba8a18741c4e7fb9b3
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04798897

Reaction notes

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