Potassium Carbonate → HCID 54278619, compound

HRID 2291723Notes

Reaction equation

HRID 2291723 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11]I)=[CH:4][CH:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][S:8][C:5]2[CH:6]=[C:13]([OH:16])[CH:2]=[CH:3][CH:4]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 21278937HCID 21278937, compound

Product 1

HCID 54278619HCID 54278619, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 12.6 g of monothioresorcinol, 31.3 g of 1-(4-chlorophenylthio)-3-iodopropane (prepared from 4-chlorothiophenol and 1-bromo-3-chloropropane followed by replacement of chlorine by iodine with sodium iodide in acetone), 16.6 g of potassium carbonate and 60 ml of acetone was stirred at room temperature for 24 hours, then the solvent was removed by distillation under reduced pressure, methylene chloride was added, the solution was washed several times with water and dried, and then 14.5 g of 3-(4-chlorophenylthiopropylthio)phenol were isolated by chromatography on silica gel using methylene chloride as mobile phase. This product was stirred together with 9.5 g of 6-chloromethyl-4-methyl-2-pyrone, 10.4 g of potassium carbonate and 60 ml of acetone at 50° C. for 31 hours, then the solvent was removed by distillation under reduced pressure, the residue was taken up in methylene chloride, and the solution was washed several times with water, dried and chromatographed on silica gel. 11.2 g of the main fraction were heated with 50 g of 2-aminopyridine at 75° C. for 65 hours, and a total of 12 g of hydroxylamine hydrochloride was added in several portions. The residue was then taken up in methylene chloride, and the organic phase was extracted by shaking with dilute hydrochloric acid and several times with water and was dried, and the solvent was removed by distillation. The residue amounted to 9.9 g. Treatment with methanol resulted in 2.7 g of pure hydroxypyridone of melting point 102° C.

Workup

  1. customthe solvent was removed by distillation under reduced pressure, methylene chloride
  2. additionwas added
  3. washthe solution was washed several times with water
  4. customdried

Sources & evidence

ORD record
ord-b20ab6af760841ab855ef7a0384719a7
Source dataset
uspto-grants-1989_01
Patent number
US04797409

Reaction notes

Loading…