4-Toluenesulfonyl chloride → 4-(2-(4-(4-p-Toluenesulfonyloxybutyl)phenyl)ethoxy) quinazoline

HRID 1479272Notes

Reaction equation

HRID 1479272 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][N:16]=2)=[CH:8][CH:7]=1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>N1C=CC=CC=1.C(OCC)(=O)C>[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=[CH:17][N:16]=3)=[CH:8][CH:7]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 444419894-(2-(4-(4-Hydroxybutyl)phenyl)ethoxy)quinazoline

Product 1

HCID 596786134-(2-(4-(4-p-Toluenesulfonyloxybutyl)phenyl)ethoxy) quinazoline

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 15 ml round bottom flask charged with 4-(2-(4-(4-hydroxybutyl)phenyl)ethoxy)quinazoline (0.25 g, 0.77 mmol) is dissolved in pyridine (5 ml). p-Toluenesulfonyl chloride (0.15 g, 0.79 mmol) is then added to it and the mixture stirred for 4 hours. The reaction mixture is diluted with ethyl acetate, washed with 5% copper sulfate solution and then with water and dried. After removing the solvent on the rotary evaporator the crude is purified by flash chromatography using silica gel (ethyl acetate/hexanes) to give the product.

Workup

  1. washwashed with 5% copper sulfate solution
  2. dry with materialwith water and dried
  3. customAfter removing the solvent
  4. customon the rotary evaporator the crude
  5. customis purified by flash chromatography
  6. customto give the product

Sources & evidence

ORD record
ord-2d0b6dc44d5e44c3bac98403d0617b9d
Source dataset
uspto-grants-2016_08
Patent number
US09408927B2

Reaction notes

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