4-Toluenesulfonyl chloride → HCID 54166309, compound

HRID 2298817Notes

Reaction equation

HRID 2298817 reaction equation
[OH:1][N:2]=[C:3]1[C:12]2[CH:11]=[N:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[OH-].[Na+]>CC(C)=O>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:1][N:2]=[C:3]2[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[CH2:6][CH2:5][CH2:4]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 86758698HCID 86758698, compound

Product 1

HCID 54166309HCID 54166309, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 8-hydroxyimino-5,6,7,8-tetrahydroisoquinoline (960 mg) and p-toluenesulfonyl chloride (1.69 g) in acetone was added 1N sodium hydroxide (8.88 ml) and the mixture was heated at 55° C. for 2 hours. The acetone was evaporated and the aqueous reaction mixture was extracted with ethyl acetate. The extract was washed with brine and dried over sodium sulfate and concentrated in vacuo to give 8-(4-methylphenylsulfonyl)oxyimino-5,6,7,8-tetrahydroisoquinoline (1.25 g).

Workup

  1. customThe acetone was evaporated
  2. extractionthe aqueous reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-220948aa67774a64b2fab67ae9b6b882
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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