4-Toluenesulfonyl chloride → 4-(2-p-Toluenesulfonyloxy-2-(4-tert-butylphenyl)ethoxy) quinazoline

HRID 1751893Notes

Reaction equation

HRID 1751893 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1)[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=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][CH:2]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:19][CH:20]=2)[CH2:3][O:4][C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=[CH:7][N:6]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 596786194-(2-Hydroxy-2-(4-tert-butylphenyl)ethoxy)quinazoline

Product 1

HCID 596786124-(2-p-Toluenesulfonyloxy-2-(4-tert-butylphenyl)ethoxy) quinazoline

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 15 ml round bottom flask is charged with 4-(2-hydroxy-2-(4-tert-butylphenyl)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-e0de04457ec2466e9c6e2b9117a5adf0
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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