Pyridine → HCID 86600391, compound

HRID 1751859Notes

Reaction equation

HRID 1751859 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][OH:25])=[CH:17][CH:16]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:32]1([CH3:42])[C:33]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>C(OCC)(=O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([S:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][S:38]([C:33]3[C:32]([CH3:42])=[CH:37][CH:36]=[CH:35][CH:34]=3)(=[O:40])=[O:39])=[CH:19][CH:20]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 68813438HCID 68813438, compound

Product 1

HCID 86600391HCID 86600391, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 15 ml round bottom flask charged with 2-tert-butyl-4-chloro-5-(4-(4-hydroxybutyl)benzyl)thio-3(2H)-pyridazinone (0.15 g, 0.39 mmol) is added pyridine. Toluenesulfonyl chloride (88.9 mg, 0.42 mmol) is then added to it and the mixture stirred for 2 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-0e63fec1a4724262aa96b07f8b09f0e3
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

Loading…