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

HRID 1381890Notes

Reaction equation

HRID 1381890 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.[S]>>[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

3

Reactant 2

HCID 5362487SulfurHCID 13518417HCID 13518417, compound

Product 1

HCID 30625322H-1,4-Thiazin-3(4H)-one, 5-methyl-6-(4-pyridinyl)-Yield 76.5%

Conditions

Temperature
140 °C

Procedure

The mixture of 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (2.14 g) and sulfur (10.7 g) was stirred at 140° C. for 1.5 hours and then cooled to room temperature. The obtained solid was extracted with methanol by using Soxhlet extractor. Methanol was evapolated to dryness, and the residue was dissolved in 50 ml of 2N hydrochloric acid. The insoluble solid was removed by filtration and the filtrate was adjusted to pH 7.2 by addition of 2N sodium hydroxide aqueous solution. The precipitates were collected by filtration and the filtrate was extracted with chloroform (20 ml×5 times) and was evaporated to dryness. The combined precipitates and the residue were recrystallized from isopropanol to give 5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one (0.88 g, yield 76.5%) as pale yellow plates.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe obtained solid was extracted with methanol
  3. dissolutionthe residue was dissolved in 50 ml of 2N hydrochloric acid
  4. customThe insoluble solid was removed by filtration
  5. additionthe filtrate was adjusted to pH 7.2 by addition of 2N sodium hydroxide aqueous solution
  6. filtrationThe precipitates were collected by filtration
  7. extractionthe filtrate was extracted with chloroform (20 ml×5 times)
  8. customwas evaporated to dryness
  9. customThe combined precipitates
  10. customthe residue were recrystallized from isopropanol

Sources & evidence

ORD record
ord-92c21e45fbc04bb59a74abb0a19c2a24
Source dataset
uspto-grants-1989_02
Patent number
US04804668

Reaction notes

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