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

HRID 1516104
Notes
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Reaction equation

HRID 1516104 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-2752d08a655041f39ce40e1b6bb45b3d
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08226929B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes