HCID 13537833, compound → HCID 13805987, compound

HRID 1285130Notes

Reaction equation

HRID 1285130 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[C:6]([CH:9]2[CH:14]=[CH:13][N:12](C(OCC(Cl)(Cl)Cl)=O)[CH:11]=[CH:10]2)[S:5][CH2:4][C:3]1=[O:23]>C(O)=O.[Zn]>[CH3:1][N:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[S:5][CH2:4][C:3]1=[O:23]

Participants

4

Reactant 1

HCID 13537833HCID 13537833, compound

Product 1

HCID 13805987HCID 13805987, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

To a solution of 4,5-dimethyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4dihydro-4-pyridinyl]-2H-1,4-thiazin-3-one (0.38 g) in formic acid (5 ml), zinc powder (1.9 g) was added and the reaction mixture was stirred at room temperature for 2 hours. Zinc powder was removed by filtration and formic acid was removed under reduced pressure. The residue was dissolved in water and neutralized with 1N aqueous sodium hydroxide. The precipitates were extracted with ethyl acetate (50 ml×6 times). The combined extracts were dried over anhydrous magnesium sulfate and ethyl acetate was removed under reduced pressure to give an oily product. The oily product was purified by silica gel column chromatography (Wakogel C-200 particles size 100-200 mesh, chloroform/methanol=20/1) to give 4,5-dimethyl-6-(4-pyridinyl)-2H-1,4-thiazin-3-one (30 mg, yield 14.3%) as a light yellow powder.

Workup

  1. customZinc powder was removed by filtration and formic acid
  2. customwas removed under reduced pressure
  3. dissolutionThe residue was dissolved in water and neutralized with 1N aqueous sodium hydroxide
  4. extractionThe precipitates were extracted with ethyl acetate (50 ml×6 times)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate and ethyl acetate
  6. customwas removed under reduced pressure
  7. customto give an oily product
  8. customThe oily product was purified by silica gel column chromatography (Wakogel C-200 particles size 100-200 mesh, chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-a46de47b0b864407b4df06ad446ea304
Source dataset
uspto-grants-1986_01
Patent number
US04565813

Reaction notes

Loading…