Water → HCID 13102693, compound

HRID 1757999Notes

Reaction equation

HRID 1757999 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].CC([O-])(C)C.[K+].CS([C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=1)(=O)=O.O>C1COCC1>[CH3:29][S:26]([C:23]1[CH:24]=[CH:25][C:20]([O:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[N:21][CH:22]=1)(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 130194-CyanophenolHCID 131026752,5-Bis(methylsulfonyl)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 13102693HCID 13102693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3.04 g of 4-cyanophenol dissolved in a 15 ml THF/15 ml DMSO mixture was added 2.86 g of t-BuOK and then 6 g of 2,5-bis(methylsulfonyl)pyridine, and the resulting mixture heated at 60° C. for 11/2 hrs. After cooling, the reaction mixture was poured into water and the solid which formed collected. Recrystallization from acetonitrile gave purified 4-((5-(methylsulfonyl)-2-pyridinyl)oxy)benzonitrile, m.p. 195°-196° C.

Workup

  1. temperatureAfter cooling
  2. customthe solid which formed
  3. customcollected
  4. customRecrystallization from acetonitrile
  5. customgave
  6. custompurified 4-((5-(methylsulfonyl)-2-pyridinyl)oxy)benzonitrile, m.p. 195°-196° C.

Sources & evidence

ORD record
ord-0d7d4f7941644859a0866593085bd4cb
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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