Pyridine → 2-tert-butyl-4-chloro-5-(2-p-toluenesulfonyloxy-1-(4-tert-butylphenyl)-1-ethyl)oxy-3(2H)-pyridazinone

HRID 1516088Notes

Reaction equation

HRID 1516088 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=2)[CH2:15][OH:16])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=C[CH:28]=1.[C:33]1(C)[C:34]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:36]=[CH:37][CH:38]=1>C(OCC)(=O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:21][CH:22]=2)[CH2:15][O:16][S:39]([C:34]2[CH:33]=[CH:38][C:37]([CH3:28])=[CH:36][CH:35]=2)(=[O:40])=[O:41])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 671003162-tert-butyl-4-chloro-5-(2-hydroxy-1-(4-tert-butylphenyl)-1-ethyl)oxy-3(2H)-pyridazinone

Product 1

HCID 866003922-tert-butyl-4-chloro-5-(2-p-toluenesulfonyloxy-1-(4-tert-butylphenyl)-1-ethyl)oxy-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 15 ml round bottom flask charged with 2-tert-butyl-4-chloro-5-(2-hydroxy-1-(4-tert-butylphenyl)-1-ethyl)oxy-3(2H)-pyridazinone (0.25 g, 0.66 mmol) is added pyridine. 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 ethyl acetate—hexanes as the eluting mixture.

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

Sources & evidence

ORD record
ord-fb07b350accc42a084e704f7d5405e01
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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