2,4,6-Trimethylpyridine → HCID 15886700, 화합물

HRID 397002노트

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HRID 397002 반응식
[NH2:1][C:2]1[C:3](=[O:14])[N:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.N1C(C)=CC(C)=CC=1C.[CH2:24]([S:31](Cl)(=[O:33])=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.C(OCC)(=O)C>[CH2:24]([S:31]([NH:1][C:2]1[C:3](=[O:14])[N:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1)(=[O:33])=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

6

반응물 3

HCID 79532,4,6-TrimethylpyridineHCID 74740Phenylmethanesulfonyl chlorideHCID 10035571Ethyl 2-(3-amino-2-oxo-1,2-dihydropyridin-1-yl)acetate

생성물 1

HCID 15886700HCID 15886700, 화합물수율 54,561.102%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A stirred solution of ethyl (3-amino-2-oxo-1,2-dihydropyridyl)acetate (40.0 g, 0.204 mole) and 2,4,6-collidine (54 mL, 0.408 mole) in tetrahydrofuran (200 mL) was cooled in an ice bath. A solution of benzylsulfonyl chloride (38.9 g, 0.204 mmole) in tetrahydrofuran (200 mL) was added over a 50-minute period. After addition was complete, the solution was stirred for 30 minutes at 0° C. The reaction mixture was diluted with ethyl acetate (1.2 L), washed with 1.0N HCl (until aqueous layer is pH 1), water (50 mL), saturated sodium bicarbonate (100 mL), and brine (2×50 mL). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was recrystallized from chloroform. 39 g of the title compound was isolated. To the mother liquor was added silica gel. The solution was swirled, then filtered through a sintered glass funnel, washing with 50% ethyl acetate in dichloromethane. The solvent was removed from the filtrate, and the residue was recrystallized from chloroform. An additional 13 g of the title compound was isolated to afford a total of 52.00 g (75% yield) of the title compound as a tan solid. Rf=0.32 (silica gel, 20% ethyl acetate in dichloromethane). m.p. 48-49° C.

후처리

  1. additionAfter addition
  2. washwashed with 1.0N HCl (until aqueous layer is pH 1), water (50 mL), saturated sodium bicarbonate (100 mL), and brine (2×50 mL)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed
  5. customThe residue was recrystallized from chloroform

출처 및 근거

ORD 기록
ord-3c1d80ffd8fe417f8d3f61bf509d0540
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608204B1

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