4-Toluenesulfonyl chloride → HCID 20193903, compound

HRID 1742591Notes

Reaction equation

HRID 1742591 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[C:9]2[CH:10]=[CH:11][N:12]=[C:13]([Cl:18])[C:14]=2[CH:15]=[CH:16][CH:17]=1)(=[O:7])=[O:6].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([O:1][CH2:2][CH2:3][NH:4][S:5]([C:8]2[C:9]3[CH:10]=[CH:11][N:12]=[C:13]([Cl:18])[C:14]=3[CH:15]=[CH:16][CH:17]=2)(=[O:6])=[O:7])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 19007135HCID 19007135, compound

Product 1

HCID 20193903HCID 20193903, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 5.74 g of N-(2-hydroxyethyl)-1-chloro-5-isoquinolinesulfonamide was successively added 80 ml of pyridine and 7.62 g of p-toluenesulfonylchloride and the mixture was stirred at 15° to 20 ° C. for 24 hours. After completion of the reaction, the mixture was cooled with 200 g of ice water and the mixture was subjected to extraction with 200 ml of dichloromethane twice. The resultant dichloromethane layer was dried over anhydrous magnesium sulfate and the residue was subjected to purification by means of a chromatography column packed with 200 g of silica gel (Wacogel C-200, manufactured by Wako Pure Chemical Industries, Ltd., Japan) using chloroform as an eluent to obtain 6.61 g of N-(2-paratoluenesulfonyloxyethyl)-1-chloro-5-isoquinolinesulfonamide (yield: 75%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was subjected to extraction with 200 ml of dichloromethane twice
  3. dry with materialThe resultant dichloromethane layer was dried over anhydrous magnesium sulfate
  4. customthe residue was subjected to purification by means of a chromatography column

Sources & evidence

ORD record
ord-5f0bf74132f24fa8beb0552c259744a5
Source dataset
uspto-grants-1994_08
Patent number
US05340811

Reaction notes

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