Sulfur → 5-methyl-6-(3-formyl-4-pyridinyl)-2H-1,4-thiazin-3(4H)-one

HRID 2292009Notes

Reaction equation

HRID 2292009 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:24])[CH2:5][S:6][C:7]=1[CH:8]1[CH:13]=[CH:12][N:11](C(OCC(Cl)(Cl)Cl)=O)[CH:10]=[C:9]1[CH:22]=[O:23].[S]>C(Cl)(Cl)Cl.CO>[CH3:1][C:2]1[NH:3][C:4](=[O:24])[CH2:5][S:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[CH:22]=[O:23]

Participants

4

Reactant 2

HCID 5362487SulfurHCID 136724205-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-3-formyl-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one

Product 1

HCID 136724125-methyl-6-(3-formyl-4-pyridinyl)-2H-1,4-thiazin-3(4H)-oneYield 10.6%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-3-formyl-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (0.5 g) and sulfur (2.5 g) was stirred at 160° C. for 3 hours. After cooling, the solid was ground and was extracted with methanol using Soxhlet extractor. Methanol was removed under reduced pressure. The residue was extracted with 40 ml of 2N hydrochloric acid. The insoluble matter was removed by filtration and the filtrate was washed with ether and the water phase was adjusted to pH 7.5 by 2N aqueous sodium hydroxide. The resulting precipitates were extracted with chloroform and were dried. Chloroform was removed under reduced pressure and the residue was purified by the preparative thin layer chromatography [TLC silica gel plate 60F254 (supplied by Merck & Co. Inc., U.S.A.), 20×20 cm, thickness 1 mm, chloroform-methanol=40:1] to give the titled compound (0.03 g, yield 10.6%) as pale yellow crystals.

Workup

  1. temperatureAfter cooling
  2. extractionwas extracted with methanol using Soxhlet extractor
  3. customMethanol was removed under reduced pressure
  4. extractionThe residue was extracted with 40 ml of 2N hydrochloric acid
  5. customThe insoluble matter was removed by filtration
  6. washthe filtrate was washed with ether
  7. customThe resulting precipitates
  8. extractionwere extracted with chloroform
  9. customwere dried
  10. customChloroform was removed under reduced pressure
  11. customthe residue was purified by the preparative thin layer chromatography [TLC silica gel plate 60F254 (supplied by Merck & Co. Inc., U.S.A.), 20×20 cm

Sources & evidence

ORD record
ord-c7af9c92cbc54c08b63ee0ff0fe3f919
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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