Potassium Hydroxide → HCID 22754232, compound

HRID 1679343Notes

Reaction equation

HRID 1679343 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[SH:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[OH-].[K+]>C(COC)OC>[F:8][C:4]1[N:3]=[C:2]([S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 739342,6-DifluoropyridineHCID 2401474-Mercaptophenol

Product 1

HCID 22754232HCID 22754232, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture comprising 69 grams (0.6 mole) of 2,6-difluoropyridine, 75.6 grams (0.6 mole) of 4-mercaptophenol and 49.5 grams (0.75 mole) of 85 percent potassium hydroxide was stirred in 300 milliliters of monoglyme for ~ 4 days at room temperature. At the end of this time, the reaction mixture was filtered to remove any solid by-products present. The filtrate was concentrated to remove most of the monoglyme and the residue mixed with 400 milliliters of 5 percent sodium hydroxide. The mixture was washed with methylene chloride and the aqueous solution acidified with concentrated hydrochloric acid. The solid 4-((6-fluoro-2-pyridyl)thio)phenol product precipitated out and was recovered by filtration, washed with water and dried. The product was recovered in a yield of 112 grams (87 percent of theoretical) and melted at 123°-124° C.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove any solid by-products present
  3. concentrationThe filtrate was concentrated
  4. customto remove most of the monoglyme
  5. additionthe residue mixed with 400 milliliters of 5 percent sodium hydroxide
  6. washThe mixture was washed with methylene chloride
  7. customThe solid 4-((6-fluoro-2-pyridyl)thio)phenol product precipitated out
  8. filtrationwas recovered by filtration
  9. washwashed with water
  10. customdried
  11. customThe product was recovered in a yield of 112 grams (87 percent of theoretical) and melted at 123°-124° C.

Sources & evidence

ORD record
ord-238b643a35c04581b6c7832d3d44800a
Source dataset
uspto-grants-1978_03
Patent number
US04080443

Reaction notes

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