4-Toluenesulfonyl chloride → HCID 22662906, compound

HRID 392510Notes

Reaction equation

HRID 392510 reaction equation
[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[N:5][CH:4]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:1][CH2:2][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[N:5][CH:4]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12746377(Isoquinolin-4-yl)methanol

Product 1

HCID 22662906HCID 22662906, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the title compound from Step A above (1.94 g, 12.2 mmoles) in anhydrous pyridine (144 mL) at 0° C. was added 4-toluenesulfonyl chloride (2.784 g, 14.6 mmoles) and the mixture was stirred at 0° C. for 2.5 h. The solution was evaporated to dryness and the product was azeotroped with toluene and then taken up in dichloromethane and washed with saturated aqueous sodium bicarbonate, filtered and evaporated to give the title compound which was used without purification in the next step.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe product was azeotroped with toluene
  3. washwashed with saturated aqueous sodium bicarbonate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-68ac3bd4dca041809c2dbf33cdbfc2db
Source dataset
uspto-grants-2004_10
Patent number
US06800636B2

Reaction notes

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