HCID 13518417, 화합물 → 2H-1,4-Thiazin-3(4H)-one, 5-methyl-6-(4-pyridinyl)-

HRID 1285126노트

반응식

HRID 1285126 반응식
[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>C(O)=O.[Zn]>[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

참가 물질

4

반응물 1

HCID 13518417HCID 13518417, 화합물

생성물 1

HCID 30625322H-1,4-Thiazin-3(4H)-one, 5-methyl-6-(4-pyridinyl)-수율 3.7%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 284Formic Acid용매

실험 절차

To a solution of 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (1 g) in formic acid (14 ml), zinc powder (1 g) was added and the reaction mixture was stirred at room temperature for 3 hours. The insoluble solid was removed by filtration. The filtrate was evaporated to dryness and the residue was dissolved in water (30 ml). The solution was adjusted to pH 7.0 by 1N aqueous sodium hydroxide. The precipitates were extracted with chloroform (although the solution was converted into an emulsion at this extracting step, the operation was facilitated by using a filter aid such as "Avicel"). The extract was dried over anhydrous magnesium sulfate and chloroform was removed under reduced pressure. The crude product was purified by the preparative thin layer chromatography [Merck TLC plate, silica gel 60F254 (particles average porous diameter 60A, Fluorescent substance Zn2SiO4 /Mn), 20×20 cm, t=1 mm, chloroform/methanol=20/1] to give 20 mg of 5-methyl-6-(4-pyridinyl)- 2H-1,4thiazin-3(4H)-one. The physical properties were as described above. The aqueous layer left after the chloroform extraction was adjusted to pH 12.5 by 1N aqueous sodium hydroxide and extracted with chloroform (50 ml×3 times). The extract was dried over anhydrous magnesium sulfate and chloroform was removed under reduced pressure. The residual solid was washed with ether and collected by filtration to give 5-methyl-6-(4-piperidinyl)-2H-1,4-thiazin-3(4H)-one (200 mg) as a light yellow powder.

후처리

  1. customThe insoluble solid was removed by filtration
  2. customThe filtrate was evaporated to dryness
  3. dissolutionthe residue was dissolved in water (30 ml)
  4. extractionThe precipitates were extracted with chloroform (although the solution
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate and chloroform
  6. customwas removed under reduced pressure
  7. customThe crude product was purified by the preparative thin layer chromatography [Merck TLC plate, silica gel 60F254 (particles average porous diameter 60A, Fluorescent substance Zn2SiO4 /Mn), 20×20 cm, t=1 mm, chloroform/methanol=20/1]

출처 및 근거

ORD 기록
ord-631d1e70ae3a4c2b895c36d6396964c6
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04565813

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