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

HRID 2292007Notes

Reaction equation

HRID 2292007 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:23])[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[Cl:22].[S]>CN(C)C=O>[CH3:1][C:2]1[NH:3][C:4](=[O:23])[CH2:5][S:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[Cl:22]

Participants

4

Reactant 2

HCID 5362487SulfurHCID 136724195-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-3-chloro-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one

Product 1

HCID 136724115-methyl-6-(3-chloro-4-pyridinyl)-2H-1,4-thiazin-3(4H)-oneYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-3-chloro-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (0.25 g) and sulfur sublimed (0.125 g) in N,N-dimethylformamide (2 ml) was stirred at 160° C. for 5 hours. The solvent was removed under reduced pressure and the residue was extracted with 2N hydrochloric acid. The insoluble matter was removed by filtration and the filtrate was washed with ether and was adjusted to pH about 7.5 by 2N aqueous sodium hydroxide. The resulting precipitates were extracted with chloroform. The extract was dried over magnesium sulfate and was evaporated to dryness. The residue was chromatographed on silica gel (Wakogel C-200) column, using chloroformmethanol (=30:1) as an eluant to give the titled compound (0.083 g, yield 57.8%) as milky white crystals.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe residue was extracted with 2N hydrochloric acid
  3. customThe insoluble matter was removed by filtration
  4. washthe filtrate was washed with ether
  5. customThe resulting precipitates
  6. extractionwere extracted with chloroform
  7. dry with materialThe extract was dried over magnesium sulfate
  8. customwas evaporated to dryness
  9. customThe residue was chromatographed on silica gel (Wakogel C-200) column

Sources & evidence

ORD record
ord-ac136fc9a17b4d2583e6617361235eb8
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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