Sulfur → HCID 13537835, compound

HRID 1285132Notes

Reaction equation

HRID 1285132 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[CH3:22].[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[CH3:22]

Participants

4

Reactant 2

HCID 5362487SulfurHCID 13537834HCID 13537834, compound

Product 1

HCID 13537835HCID 13537835, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

The mixture of 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-3-methyl-1,4dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (250 mg) and sulfur (125 mg) in N,N-dimethylformamide (2 ml) was heated at 160° C. for 1 hour. N,N-dimethylformamide was removed under reduced pressure and residue was extracted with 2N hydrochloric acid. The insoluble solid was removed by filtration and filtrate was washed with ether. The aqueous solution was adjusted to pH 7.2 by 2N aqueous sodium hydroxide. The precipitates were extracted with chloroform and the extract was dried over anhydrous magnesium sulfate. Chloroform was removed under reduced pressure and residue was purified by silica gel column chromatography (Wakogel C-200, chloroform/methanol=20/1) to give 118 mg of 5-methyl-6-(3-methyl-4-pyridinyl)-2H-1,4-thiazin-3(4H)-one as pale-brown crystal.

Workup

  1. customN,N-dimethylformamide was removed under reduced pressure and residue
  2. extractionwas extracted with 2N hydrochloric acid
  3. customThe insoluble solid was removed by filtration and filtrate
  4. washwas washed with ether
  5. extractionThe precipitates were extracted with chloroform
  6. dry with materialthe extract was dried over anhydrous magnesium sulfate
  7. customChloroform was removed under reduced pressure and residue
  8. customwas purified by silica gel column chromatography (Wakogel C-200, chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-174ae27847a344b9832d723d00b8ce5d
Source dataset
uspto-grants-1986_01
Patent number
US04565813

Reaction notes

Loading…