Sodium Iodide → HCID 13938754, compound

HRID 2291721Notes

Reaction equation

HRID 2291721 reaction equation
ON1[C:7]([CH2:8][S:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[CH:11]=2)=[CH:6][C:5]([CH3:28])=[CH:4][C:3]1=[O:29].ClCC1[O:37]C(=O)C=C(C)C=1.C(=O)([O-])[O-].[K+].[K+].ClCC1C2C(=CC=CC=2)C=CC=1.[I-].[Na+]>CN(C)C=O.CC(C)=O.C(Cl)Cl>[CH3:28][C:5]1[CH:6]=[C:7]([CH2:8][S:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[CH:11]=2)[O:37][C:3](=[O:29])[CH:4]=1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 68451-ChloromethylnaphthaleneHCID 11430Potassium Carbonate2×HCID 13938746HCID 13938746, compoundHCID 144779056-(Chloromethyl)-4-methyl-2H-pyran-2-one

Product 1

HCID 13938754HCID 13938754, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxy-4-methyl-6-[3-(1-naphthylmethoxy)phenylthiomethyl]-2-pyridone 26 g of monothioresorcinol and 31.8 g of 6-chloromethyl-4-methyl-2-pyrone were dissolved in 100 ml of dimethylformamide and, while stirring and cooling in ice, 38 g of powdered potassium carbonate were added within 30 minutes, then the mixture was stirred at 0° C. for 4 hours and at room temperature for 16 hours, then 300 ml of methylene chloride were added, and the organic phase was extracted by shaking three times with water, separated off and dried, and the solvent was removed by distillation. The residue was recrystallized from methanol, and 44 g of 6-(3-hydroxyphenylthiomethyl)-4-methyl-2-pyrone, compound (C) of melting point 129 ° C., were obtained. 8.9 g of 1-chloromethylnaphthalene were added to a solution of 8 g of sodium iodide in 200 ml of acetone, the mixture was stirred at room temperature for 16 hours, and then 12.4 g of compound C were dissolved in the mixture, which was cooled to 0° C. and 6.9 g of powdered potassium carbonate were added in portions within 5 hours. After a total reaction time of 79 hours at 0° C., the solvent was removed by distillation under waterpump vacuum, the residue was taken up in methylene chloride, and the solution was washed with water, separated off, dried and concentrated, and the product as chromatographed on a column containing silica gel and using methylene chloride as mobile phase, and the main fractions were recrystallized from methanol. 9 g of pure 4-methyl-6-[3-(1-naphthylmethoxy)phenylthiomethyl]-2-pyrone of melting point 139° C. were obtained.

Workup

  1. temperaturecooling in ice
  2. stirringthe mixture was stirred at 0° C. for 4 hours and at room temperature for 16 hours
  3. extractionthe organic phase was extracted
  4. stirringby shaking three times with water
  5. customseparated off
  6. customdried
  7. customthe solvent was removed by distillation
  8. customThe residue was recrystallized from methanol, and 44 g of 6-(3-hydroxyphenylthiomethyl)-4-methyl-2-pyrone, compound (C) of melting point 129 ° C.
  9. customwere obtained
  10. stirringthe mixture was stirred at room temperature for 16 hours
  11. customAfter a total reaction time of 79 hours at 0° C., the solvent was removed by distillation under waterpump vacuum
  12. washthe solution was washed with water
  13. customseparated off
  14. customdried
  15. concentrationconcentrated
  16. customthe product as chromatographed on a column
  17. additioncontaining silica gel
  18. customthe main fractions were recrystallized from methanol

Sources & evidence

ORD record
ord-6e5397cf767246c7bc9ea10e863069dc
Source dataset
uspto-grants-1989_01
Patent number
US04797409

Reaction notes

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