4-Toluenesulfonyl chloride → HCID 1712496, compound

HRID 2058111Notes

Reaction equation

HRID 2058111 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>O>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([O:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 79713-HydroxypyridineHCID 14798Sodium Hydroxide

Product 1

HCID 1712496HCID 1712496, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Equimolar portions (0.106 moles) of 3-hydroxypyridine, sodium hydroxide and p-toluenesulfonyl chloride were combined in 100 ml of water and stirred at 50° C. for 2.5 hours. The aqueous solution was extracted with chloroform, dried over sodium sulfate and distilled to yield an oil which crystallized on standing. Recrystallization from cyclohexane yielded a white solid, mp 76°-78° C., lit. mp 79° C.

Workup

  1. extractionThe aqueous solution was extracted with chloroform
  2. dry with materialdried over sodium sulfate
  3. distillationdistilled
  4. customto yield an oil which
  5. customcrystallized
  6. customRecrystallization from cyclohexane
  7. customyielded a white solid, mp 76°-78° C., lit. mp 79° C.

Sources & evidence

ORD record
ord-54f8d1de04464e289a3eb6d98fa36fa5
Source dataset
uspto-grants-1980_07
Patent number
US04215003

Reaction notes

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