HCID 13518417, compound → 2H-1,4-Thiazin-3(4H)-one, 5-methyl-6-(4-pyridinyl)-

HRID 1381891Notes

Reaction equation

HRID 1381891 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:22])[CH2:5][S:6][C:7]=1[CH:8]1[CH:13]=[CH:12][N:11](C(OCC(Cl)(Cl)Cl)=O)[CH:10]=[CH:9]1>C(O)=O.[Zn]>[CH3:1][C:2]1[NH:3][C:4](=[O:22])[CH2:5][S:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 13518417HCID 13518417, compound

Product 1

HCID 30625322H-1,4-Thiazin-3(4H)-one, 5-methyl-6-(4-pyridinyl)-Yield 37.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

Zinc powder (1 g) was added to a stirred solution of 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (1 g) in formic acid (14 ml), and the reaction mixture was stirred at room temperature for 3 hours. The insoluble solid was removed by filtration. The filtrate was evaporated to dryness and the residue was dissolved in water (30 ml). The solution was adjusted to pH 7.0 by addition of 1N sodium hydroxide aqueous solution. The precipitates were extracted with chloroform (although the solution was converted into an emulsion at this extracting step, the operation was facilitated by using a filter aid such as "Avicel"). The extract was dried over anhydrous magnesium sulfate and was evaporated under reduced pressure. The crude product was purified by the preparative thin layer chromatography [Merck TLC plate, silica gel 60F254 t (particles average porous diameter 60A, Fluorescent substance Zn2SiO4 /Mn), 20×20 cm, t=1 mm, chloroform/methanol= 20/1] to give 200 mg of 5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one. The physical properties were as described above.

Workup

  1. customThe insoluble solid was removed by filtration
  2. customThe filtrate was evaporated to dryness
  3. dissolutionthe residue was dissolved in water (30 ml)
  4. additionThe solution was adjusted to pH 7.0 by addition of 1N sodium hydroxide aqueous solution
  5. extractionThe precipitates were extracted with chloroform (although the solution
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. customwas evaporated under reduced pressure
  8. customThe crude product was purified by the preparative thin layer chromatography [Merck TLC plate, silica gel 60F254 t (particles average porous diameter 60A, Fluorescent substance Zn2SiO4 /Mn), 20×20 cm, t=1 mm, chloroform/methanol= 20/1]

Sources & evidence

ORD record
ord-0cf0b7a4d3954a1ab6b893ce0ec69340
Source dataset
uspto-grants-1989_02
Patent number
US04804668

Reaction notes

Loading…