Pyridinium chloride → HCID 20368388, compound

HRID 616638Notes

Reaction equation

HRID 616638 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([C:7]1[S:8][C:9]2[CH:21]=[C:20]([O:22]C)[CH:19]=[CH:18][C:10]=2[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:6].Cl.N1C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([C:7]1[S:8][C:9]2[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:10]=2[C:11]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:6]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 20368321HCID 20368321, compound

Product 1

HCID 20368388HCID 20368388, compoundYield 39%

Procedure

A mixture of 10.9 g. of the product from Example 16 and 33.6 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, and the resulting solid was collected. The solid was washed with water and dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The ethyl acetate solution then was filtered and evaporated. The residue was recrystallized from a mixture of methanol and a minimum of acetone to give 5.07 g. (39 percent) of the title compound, m.p. 215° C.

Workup

  1. additionA mixture of 10.9 g
  2. customthe resulting solid was collected
  3. washThe solid was washed with water
  4. dissolutiondissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe ethyl acetate solution then was filtered
  8. customevaporated
  9. customThe residue was recrystallized from a mixture of methanol
  10. customa minimum of acetone to give 5.07 g

Sources & evidence

ORD record
ord-8d22e304faff456cbc9707f690ff7bfb
Source dataset
uspto-grants-1978_02
Patent number
US04075227

Reaction notes

Loading…