Sulfur → 103807-33-6

HRID 2292023Notes

Reaction equation

HRID 2292023 reaction equation
[S].[CH3:2][CH:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([CH:11]2[CH:16]=[CH:15][N:14](C(OCC(Cl)(Cl)Cl)=O)[CH:13]=[CH:12]2)[S:4]1>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:2][CH:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:4]1

Participants

5

Reactant 2

HCID 5362487SulfurHCID 13805985HCID 13805985, compound

Product 1

HCID 11971509103807-33-6Yield 52%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Sulfur sublimed (0.7 g) was added to a solution of 2,5-dimethyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (1.5 g) in dimethylformamide (20 ml) and the mixture was stirred at 140° C. for 2 hours. Then, the mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was dissolved in 2N hydrochloric acid and the insoluble matter was removed by filtration. The filtrate was adjusted to pH 7-8 by 2N aqueous sodium hydroxide. The precipitated crude crystals were chromatographed on silica gel (Wakogel C-200) column, using chloroform-methanol (=20:1) as an eluant to give pale yellow crystals. These crude crystals were dissolved in chloroform, were washed with water and were dried over magnesium sulfate. The solvent was removed under reduced pressure to give the titled compound (0.43 g, yield 52%) as white crystals.

Workup

  1. temperatureto cool to ambient temperature
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in 2N hydrochloric acid
  4. customthe insoluble matter was removed by filtration
  5. customThe precipitated crude crystals
  6. customwere chromatographed on silica gel (Wakogel C-200) column
  7. customto give pale yellow crystals
  8. washwere washed with water
  9. dry with materialwere dried over magnesium sulfate
  10. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a70808b5b08e4502b5eff0b53d09a608
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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