Pyridinium chloride → HCID 20368375, compound

HRID 616630Notes

Reaction equation

HRID 616630 reaction equation
[C:1]([C:9]1[S:10][C:11]2[CH:23]=[C:22]([O:24]C)[CH:21]=[CH:20][C:12]=2[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1>>[C:1]([C:9]1[S:10][C:11]2[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:12]=2[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 15406406HCID 15406406, compound

Product 1

HCID 20368375HCID 20368375, compoundYield 88%

Procedure

A mixture of 2.5 g. (0.0073 mole) of the product from Example 5 and 10 g. of pyridine hydrochloride was refluxed in a 220° C. oil bath for 1.5 hours. The hot reaction mixture then was poured over an ice-water mixture in a blender, and the resulting yellow crystals were collected. The crystals then were dissolved in ethyl acetate, and the ethyl acetate solution was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The ethyl acetate solution then was filtered over silica, and the silica was washed with ethyl acetate which was added to the original ethyl acetate solution. The ethyl acetate was evaporated and the resulting residue was crystallized from methanol to give 2.1 g. (88 percent) of the title compound as yellow crystals, m.p. 187°-190° C. The product was recrystallized from methanol to give a purified product having melting point 191°-191.5° C.

Workup

  1. additionA mixture of 2.5 g
  2. customthe resulting yellow crystals were collected
  3. dissolutionThe crystals then were dissolved in ethyl acetate
  4. washthe ethyl acetate solution was washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe ethyl acetate solution then was filtered over silica
  7. washthe silica was washed with ethyl acetate which
  8. additionwas added to the original ethyl acetate solution
  9. customThe ethyl acetate was evaporated
  10. customthe resulting residue was crystallized from methanol
  11. customto give 2.1 g

Sources & evidence

ORD record
ord-3bcbd475cfa740a689e7bc6298c60e53
Source dataset
uspto-grants-1978_02
Patent number
US04075227

Reaction notes

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